Simple oxidative functionalized of alkyl aryl ketones

ABSTRACT

The present invention refers to a process for reacting an alkyl aryl ketone obtaining thereby the corresponding aryl oxirane or α-functionalized alkyl aryl ketal, the aryl oxirane or α-functionalized alkyl aryl ketal obtained by the process as well as the α-functionalized ketone obtained by the process.

FIELD OF THE INVENTION

The present invention refers to a process for reacting an alkyl arylketone obtaining thereby the corresponding aryl oxirane orα-functionalized alkyl aryl ketal, the aryl oxirane or α-functionalizedalkyl aryl ketal obtained by the process as well as the α-functionalizedketone obtained by the process.

BACKGROUND OF THE INVENTION

Photopolymerization processes have attained major importance in a largenumber of applications, for example in overprint coatings, printinginks, in the manufacture of electronic printed circuit boards andprinting plates, and in the coating of various substrates, such as wood,plastics, paper, glass or metal, due their tremendous advantages overconventional hardening systems. One advantage of photo-curing by UVirradiation in the presence of photoinitiators is the great speed.However, the speed is heavily dependent on the photoinitiator used.Among the most effective photoinitiators are α-hydroxylated ketones asdescribed e.g. in German Patent No. 2,722,264 and U.S. Pat. No.4,740,624. Further methods for the α-functionalization of ketones aredescribed e.g. in Gary Jing Chuang et al., “A Dinuclear PalladiumCatalyst for α-Hydroxylation of Carbonyls with O₂”, J. Am. Chem. Soc.133, 1760-1762 (2011). Chengqun Chen et al. “An Efficient Method for theSynthesis of α-Hydroxyalkyl Aryl Ketones”, Synthesis 2008, No. 20,3205-3208; Marek Koprowski et al., “Asymmetric oxidation of enolphosphates to α-hydroxy ketones by (salen)manganese(III) complex;Effects of the substitution pattern of enol phosphates on thestereochemistry of oxygen transfer”, Tetrahedron 62 12363-12374 (2006);Franklin A. Davis et al., “Oxidation of Silyl Enol Ethers Using2-Sulfonyloxaziridines; Synthesis of α-Siloxy Epoxides and α-HydroxyCarbonyl Compounds”, J. Org. Chem. 52, 954-955 (1987); Yu-Feng Liang etal., “Highly Efficient C—H Hydroxylation of Carbonyl Compounds withOxygen under Mild Conditions”, Angew. Chem. 2014, 126, 558-562; Yu-FengLiang et al., “I₂- or NBS-Catalyzed Highly Efficient aHydroxylation ofKetones with Dimethyl Sulfoxide”, Org. Lett. 17, 876-879 (2015);Bang-Chi Chen et al., “α-hydroxylation of enolates and silyl enolethers”, Organic Reactions, Vol. 62, 2003, published by John Wiley &Sons, Inc.

However, the processes used for the preparation of α-hydroxylatedketones show a number of disadvantages. In particular, it is to be notedthat the α-hydroxylated ketones are prepared by complex reactionsresulting in a great variety of unwanted intermediate products andby-products which reduce the yield and purity of the desiredα-hydroxylated ketone and which are of no commercial interest.Furthermore, often elaborate purification steps are required.Accordingly, the well-known processes of the prior art are quite complexas well as time- and chemical-consuming.

Therefore, there is a continuous need in the art for providing a processfor the preparation of α-functionalized ketones avoiding the forgoingdisadvantages. Furthermore, it is desirable to provide a process for thepreparation of α-functionalized ketones which uses cheap startingmaterials. Furthermore, it is desirable to provide a process for thepreparation of α-functionalized ketones which avoids complex processingand elaborate purification steps for obtaining the desiredα-functionalized ketones. In addition thereto, it is desirable toprovide a process for the preparation of α-functionalized ketones whichavoids the formation of unwanted by-products and thus increases theyield and purity of the desired α-functionalized ketones. Furthermore,it is desirable to provide a process which allows the preparation ofdefined intermediate products, such as alkyl aryl ketals and/or aryloxiranes.

Accordingly, it is an object of the present invention to provide aprocess for the preparation of α-functionalized ketones. It is an evenfurther object of the present invention to provide a process for thepreparation of α-functionalized ketones using cheap starting materialsand without complex processing or elaborate purification steps forobtaining the desired α-functionalized ketones. It is an even furtherobject of the present invention to provide a process for the preparationof α-functionalized ketones which increases the yield and purity of thedesired α-functionalized ketones. It is another object of the presentinvention to provide a process which allows the preparation of definedintermediate products, such as alkyl aryl ketals and/or aryl oxiranes.

SUMMARY OF THE INVENTION

The foregoing and other objects are solved by the subject-matter of thepresent invention.

According to a first aspect of the present invention, a process forreacting an alkyl aryl ketone of the general formula I,

wherein R₁ and R₂ are the same or different and are independentlyselected from H, linear or branched C₁-C₈-alkyl, C₃-C₈-cycloalkyl,linear or branched C₂-C₈-alkenyl, C₅-C₈-cycloalkenyl, linear or branchedC₂-C₈-alkynyl, C₆-C₁₄-aryl or form C₃-C₁₂-cycloalkyl orC₅-C₁₂-cycloalkenyl together with the connecting C atom;

R₃, R₄, R₅, R₆ and R₇ are the same or different and are independentlyselected from H, linear or branched C₁-C₈-alkyl, linear or branchedC₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl,C₆-C₁₄-aryl, C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxy,C₉-C₁₅-alkenylarylalkoxy, N(R₈)₂ or SR₈ with R₈ being selected fromlinear or branched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl,C₆-C₁₄-aryl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, or R₈form a C₃-C₉-alicyclic system together with the connecting N atom,optionally one or more carbon atoms are replaced with O, or two adjacentR form an aromatic system together with the benzene ring of formula I;

with an at least partially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene,and a base selected from alkali metal C₁-C₈-alkoxide, earth alkali metalC₁-C₈-alkoxide and mixtures thereof, obtaining thereby the correspondingaryl oxirane or α-functionalized alkyl aryl ketal.

The inventors surprisingly found out that such a process is suitable forthe preparation of α-functionalized ketones by the use of cheap startingmaterials and which avoids complex processing and elaborate purificationsteps for obtaining the desired α-functionalized ketones. The processthus increases the yield and purity of the desired α-functionalizedketones. Furthermore, the process allows the preparation of definedintermediate products, i.e. aryl oxiranes and α-functionalized alkylaryl ketals, which are of commercial interest.

Advantageous embodiments of the inventive process are defined in thecorresponding sub-claims.

According to one embodiment, R₁ and R₂ are the same.

According to another embodiment, R₁ and R₂ are selected from H andlinear or branched C₁-C₈-alkyl, preferably linear or branchedC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl and mostpreferably linear C₁-C₃-alkyl.

According to yet another embodiment, R₁ and R₂ are different and areindependently selected from H and linear or branched C₁-C₈-alkyl,preferably linear or branched C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl and most preferably linear C₁-C₃-alkyl.

According to one embodiment, R₁ and R₂ form C₄-C₁₀-cycloalkyl,preferably C₄-C₈-cycloalkyl, and most preferably C₆-cycloalkyl, togetherwith the connecting C atom.

According to another embodiment, R₃, R₄, R₅, R₆ and R₇ are the same.According to yet another embodiment, R₃, R₄, R₅, R₆ and R₇ are selectedfrom H and linear or branched C₁-C₈-alkyl, preferably linear or branchedC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl and mostpreferably linear C₁-C₃-alkyl.

According to one embodiment, R₃, R₄, R₅, R₆ and R₇ are different and atleast one of them is selected from linear or branched C₁-C₈-alkyl,linear or branched C₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy,C₉-C₁₅-alkenylarylalkoxy or N(R₈)₂ or SR₈ with R₈ being selected fromlinear or branched C₁-C₈-alkyl or linear or branched C₂-C₈-alkenyl or R₈form a C₃-C₉-alicyclic system together with the connecting N atom.

According to another embodiment, one of R₃, R₄, R₅, R₆ and R₇ is linearor branched C₂-C₈-alkenyl, preferably C₂-C₆-alkenyl and most preferablyC₂-C₃-alkenyl; C₁-C₈-alkoxy, preferably C₁-C₆-alkoxy and most preferablyC₁-C₃-alkoxy; C₂-C₈-alkenyloxy, preferably C₂-C₆-alkenyloxy and mostpreferably C₃-C₅-alkenyloxy; C₉-C₁₅-alkenylarylalkoxy, preferablyC₉-C₁₂-alkenylarylalkoxy and most preferably C₉-C₁₀-alkenylarylalkoxy;or N(R₈)₂ or SR₈ with R₈ being selected from linear or branchedC₁-C₈-alkyl or linear or branched C₂-C₈-alkenyl or R₈ form aC₃-C₉-alicyclic system together with the connecting N atom; and theremaining ones are independently selected from H and linear or branchedC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, more preferablylinear or branched C₁-C₄-alkyl and most preferably linear C₁-C₃-alkyl.

According to yet another embodiment, two or three of R₃, R₄, R₅, R₆ andR₇ are linear or branched C₂-C₈-alkenyl, preferably C₂-C₆-alkenyl andmost preferably C₂-C₃-alkenyl; C₁-C₈-alkoxy, preferably C₁-C₆-alkoxy andmost preferably C₁-C₃-alkoxy; C₂-C₈-alkenyloxy, preferablyC₂-C₆-alkenyloxy and most preferably C₃-C₀-alkenyloxy; andC₉-C₁₅-alkenylarylalkoxy, preferably C₉-C₁₂-alkenylarylalkoxy and mostpreferably C₉-C₁₀-alkenylarylalkoxy, and the remaining ones areindependently selected from H and linear or branched C₁-C₈-alkyl,preferably linear or branched C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl and most preferably linear C₁-C₃-alkyl.

According to one embodiment, R₃ and R₄ or R₄ and R₅ form an aromaticsystem together with the benzene ring of formula I, preferably abicyclic, tricyclic or tetracyclic aromatic system, more preferably anaromatic system selected from a naphthyl, anthracenyl and phenanthrenylsystem.

According to another embodiment, one of the remaining R is linear orbranched C₂-C₈-alkenyl, preferably C₂-C₆-alkenyl and most preferablyC₂-C₃-alkenyl; C₂-C₈-alkenyloxy, preferably C₂-C₆-alkenyloxy and mostpreferably C₃-C₅-alkenyloxy; and C₉-C₁₅-alkenylarylalkoxy, preferablyC₉-C₁₂-alkenylarylalkoxy and most preferably C₉-C₁₀-alkenylarylalkoxy;and the remaining ones are independently selected from H and linear orbranched C₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, morepreferably linear or branched C₁-C₄-alkyl and most preferably linearC₁-C₃-alkyl.

According to yet another embodiment, the at least partially halogenatedC₂-C₈-alkane and/or C₂-C₈-alkene is fully halogenated, preferably the atleast partially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene is selectedfrom hexachloroethane, tetrachoroethylene and mixtures thereof.

According to one embodiment, the base is selected from the groupcomprising sodium C₁-C₆-alkoxide, preferably sodium C₁-C₄-alkoxide andmost preferably sodium C₁-C₂-alkoxide; lithium C₁-C₆-alkoxide,preferably lithium C₁-C₄-alkoxide and most preferably lithiumC₁-C₂-alkoxide; potassium C₁-C₆-alkoxide, preferably potassiumC₁-C₄-alkoxide and most preferably potassium C₁-C₂-alkoxide; andmixtures thereof.

According to another embodiment, the base is in form of an aqueoussolution or the base is provided in an organic solvent, preferably theorganic solvent is selected from the group comprising methanol, ethanol,n-propanol, tert.-butanol, dichloromethane, tetrachloroethylene,tetrahydrofuran, ethyl acetate, acetone, N,N-dimethylformamide, dimethylsulfoxide, dioxane, such as 1,3-dioxane or 1,4-dioxane,1,2-dimethoxyethane, diethyleneglycol dimethyl ether, triethyleneglycoldimethyl ether and mixtures thereof.

According to yet another embodiment, the process is carried out at atemperature in the range from 0 to 120° C., preferably in the range from12 to 80° C., more preferably in the range from 15 to 50° C., and mostpreferably in the range from 15 to 30° C.

According to one embodiment, the process is carried out in an organicsolvent, preferably the organic solvent is selected from the groupcomprising methanol, ethanol, n-propanol, tert.-butanol,dichloromethane, tetrachloroethylene, tetrahydrofuran, ethyl acetate,acetone, N,N-dimethylformamide, dimethyl sulfoxide, dioxane, such as1,3-dioxane or 1,4-dioxane, 1,2-dimethoxyethane, diethyleneglycoldimethyl ether, triethyleneglycol dimethyl ether and mixtures thereof.

According to one embodiment, the process comprises a further step ofcontacting the aryl oxirane obtained by the process under phase-transferconditions with a base selected from the group comprising alkali metalhydroxide, earth alkali metal hydroxide, alkali metal C₁-C₈-alkoxide,earth alkali metal C₁-C₈-alkoxide and mixtures and a compound selectedfrom HOR₉, HNHR₉ or HNR₁₀R₁₁ with R₉, R₁₀ and R₁₁ being independentlyselected from H, linear or branched C₁-C₈-alkyl, linear or branchedC₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkoxy, C₆-C₁₄-aryl, C₇-C₁₅-arylalkyl, C₇-C₁₅-arylalkoxy,C₉-C₁₅-alkenylarylalkoxy, C₉-C₁₅-alkenylarylalkyl; or R₁₀ and R₁₁ form aC₃-C₉-alicyclic system together with the connecting N or C atom,optionally one or more carbon atoms are replaced with O.

According to another embodiment, the step is carried out in the presenceof a phase-transfer catalyst, preferably the phase-transfer catalyst isselected from a quaternary ammonium salt, tetraalkylphosphoniumchloride, tetraalkylphosphonium bromide and mixtures thereof, preferablythe phase-transfer catalyst is a tetraalkylammonium salt or atrialkylarylammonium salt, more preferably the phase-transfer catalystis selected from the group comprising benzyltrimethylammonium hydroxide,benzyltriethylammonium chloride, tetrabutylammonium chloride,tetrabutylammonium bromide, tetrabutylammonium hydrogensulfate,tetrabutylammonium hydroxide, methyltrioctylammonium chloride, cetylpyridinium and mixtures thereof.

According to yet another embodiment, the process comprises a furtherstep of contacting the α-functionalized alkyl aryl ketal obtained by theprocess with an acid, preferably an acid selected from the groupcomprising hydrochloric acid, acetic acid, phosphoric acid, sulfuricacid, citric acid, toluenesulfonic acid, methanesulfonic acid,chloroacetic acid, trichloroacetic acid, tartaric acid, succinic acid,maleic acid, fumaric acid, lactic acid, malic acid, propionic acid,butyric acid and mixtures thereof.

According to one embodiment, an α-functionalized ketone of the generalformula II is obtained,

wherein R₁, R₂, R₃, R₄, R₅, R₆ and R₇ are as defined above; and Z isselected from OR₉, NHR₉ and NR₁₀R₁₁ with R₉, R₁₀ and R₁₁ beingindependently selected from H, linear or branched C₁-C₈-alkyl, linear orbranched C₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy, C₆-C₁₄-aryl, C₇-C₁₅-arylalkyl,C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, C₉-C₁₅-alkenylarylalkyl; orR₁₀ and R₁₁ form a C₃-C₉-alicyclic system together with the connecting Nor C atom, optionally one or more carbon atoms are replaced with O.

According to another embodiment, Z is OR₉ with R₉ being selected from H,linear or branched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl,C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy,C₇-C₁₅-arylalkoxy and C₉-C₁₅-alkenylarylalkoxy, preferably R₉ is H or Zis NR₁₀R₁₁ with R₁₀ and R₁₁ being independently selected from H, linearor branched C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₆-C₁₄-aryl, or R₁₀ and R₁₁form a C₃-C₆-alicyclic system together with the connecting N atom,optionally one or more carbon atoms are replaced with O, preferably R₁₀and R₁₁ form a C₅-C₆-alicyclic system together with the connecting Natom and one or more carbon atoms are replaced with O.

According to a further aspect of the present invention, an aryl oxiraneor α-functionalized alkyl aryl ketal obtained by a process, as definedherein, is provided. According to another aspect of the presentinvention, an α-functionalized ketone obtained by a process as definedherein, is provided.

In the following, the details and preferred embodiments of the inventiveprocess for reacting an alkyl aryl ketone will be described in moredetail. It is to be understood that these technical details andembodiments also apply to the inventive products, as far as applicable.

DETAILED DESCRIPTION OF THE INVENTION

A process for reacting an alkyl aryl ketone is provided. In particular,a process for reacting an alkyl aryl ketone of the general formula I,

wherein R₁ and R₂ are the same or different and are independentlyselected from H, linear or branched C₁-C₈-alkyl, C₃-C₈-cycloalkyl,linear or branched C₂-C₈-alkenyl, C₅-C₈-cycloalkenyl, linear or branchedC₂-C₈-alkynyl, C₆-C₁₄-aryl or form C₃-C₁₂-cycloalkyl orC₅-C₁₂-cycloalkenyl together with the connecting C atom;

R₃, R₄, R₅, R₆ and R₇ are the same or different and are independentlyselected from H, linear or branched C₁-C₈-alkyl, linear or branchedC₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl,C₆-C₁₄-aryl, C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxy,C₉-C₁₅-alkenylarylalkoxy, N(R₈)₂ or SR₈ with R₈ being selected fromlinear or branched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl,C₆-C₁₄-aryl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, or R₈form a C₃-C₉-alicyclic system together with the connecting N atom,optionally one or more carbon atoms are replaced with O, or two adjacentR form an aromatic system together with the benzene ring of formula I;

with an at least partially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene,and a base selected from alkali metal C₁-C₈-alkoxide, earth alkali metalC₁-C₈-alkoxide and mixtures thereof, obtaining thereby the correspondingaryl oxirane or α-functionalized alkyl aryl ketal, is provided.

Thus, it is appreciated that an alkyl aryl ketone of the general formulaI is used as starting material,

wherein R₁ and R₂ are the same or different and are independentlyselected from H, linear or branched C₁-C₈-alkyl, C₃-C₈-cycloalkyl,linear or branched C₂-C₈-alkenyl, C₅-C₈-cycloalkenyl, linear or branchedC₂-C₈-alkynyl, C₆-C₁₄-aryl, or form C₃-C₁₂-cycloalkyl orC₅-C₁₂-cycloalkenyl together with the connecting C atom;

R₃, R₄, R₅, R₆ and R₇ are the same or different and are independentlyselected from H, linear or branched C₁-C₈-alkyl, linear or branchedC₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl,C₆-C₁₄-aryl, C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxy,C₉-C₁₅-alkenylarylalkoxy, N(R₈)₂ or SR₈ with R₈ being selected fromlinear or branched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl,C₆-C₁₄-aryl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, or R₈form a C₃-C₉-alicyclic system together with the connecting N atom,optionally one or more carbon atoms are replaced with O, or two adjacentR form an aromatic system together with the benzene ring of formula I.

As regards R₁ and R₂ in the general formula I, it is to be noted thatthey can be the same or different. Preferably, R₁ and R₂ are the same ordifferent and are independently selected from H, linear or branchedC₁-C₈-alkyl, C₃-C₈-cycloalkyl, linear or branched C₂-C₈-alkenyl,C₅-C₈-cycloalkenyl, linear or branched C₂-C₈-alkynyl, C₆-C₁₄-aryl orform C₃-C₁₂-cycloalkyl or C₅-C₁₂-cycloalkenyl together with theconnecting C atom.

The term “linear or branched C₁-C₈-alkyl” in the meaning of the presentinvention refers to a linear or branched chain alkyl group having 1 to 8carbon atoms, and includes, for example, methyl, ethyl, propyl,isopropyl, butyl, isobutyl, secondary butyl, tertiary butyl, pentyl,isopentyl, neopentyl, hexyl, heptyl, octyl, 2-ethylhexyl and1,1,3,3-tetramethylbutyl.

The term “C₃-C₈-cycloalkyl” in the meaning of the present inventionrefers to a cyclic alkyl having 3 to 8 carbon atoms, and includes, forexample, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, andcycloheptyl.

The term “C₅-C₈-cycloalkenyl” in the meaning of the present inventionrefers to a cyclic alkenyl having 3 to 8 carbon atoms, and includes, forexample, cyclopentenyl, cyclohexenyl, and cycloheptenyl.

The term “linear or branched C₂-C₈-alkenyl” in the meaning of thepresent invention refers to a linear or branched chain alkenyl grouphaving 2 to 8 carbon atoms, and includes, for example, ethenyl, propenylsuch as 2-propenyl, butenyl, triisobutenyl, pentenyl, hexenyl, heptenyland octenyl. The term “alkenyl” in the meaning of the present inventionincludes the cis and trans isomers.

The term “linear or branched C₂-C₈-alkynyl” in the meaning of thepresent invention refers to a linear or branched chain alkynyl grouphaving 2 to 8 carbon atoms, and includes, for example, ethynyl, propynylsuch as 1-propynyl or 2-propynyl, e.g. propargyl, butynyl, pentynyl,hexynyl, heptynyl and octynyl.

The term “C₆-C₁₄-aryl” in the meaning of the present invention refers toa group containing one or more 6-membered unsaturated hydrocarbonring(s), wherein the unsaturation is represented formally by conjugateddouble bonds and which may optionally be substituted at one or morecarbon atoms of such ring(s) by independently selected alkyl groups.Thus, the term “C₆-C₁₄-aryl” preferably includes (unsubstituted)C₆-C₁₀-aryl and C₆-C₁₄-alkylaryl. Suitable examples include, forexample, phenyl, naphthyl, methylphenyl, dimethoxyphenyl,5-isopropyl-2-methylphenyl, methylphenyl, ethylphenyl, dimethylphenyl,t-butylphenyl, methylnaphthyl and dimethylnaphthyl.

The term “form C₃-C₁₂-cycloalkyl together with the connecting C atom” inthe meaning of the present invention refers to a mono-, bi- or tricyclicalkyl having 3 to 12 carbon atoms, and includes, for example,cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, norbornyland adamantyl.

The term “form C₅-C₁₂-cycloalkenyl together with the connecting C atom”in the meaning of the present invention refers to a mono-, bi- ortricyclic alkenyl having 5 to 12 carbon atoms, and includes, one ormore, preferably one, double bond(s). Suitable examples include, forexample, cyclopentenyl, cyclohexenyl, cyclohexadienyl and cycloheptenyl.It is appreciated that the double bond of the C₅-C₁₂-cycloalkenyl islocated such that an α,β-unsaturated carbonyl compound is not formed.Thus, R₁ and R₂ in the general formula I can form C₅-C₁₂-cycloalkenyltogether with the connecting C atom with the proviso that noα,β-unsaturated carbonyl compound is formed.

In one embodiment, R₁ and R₂ are the same or different and areindependently selected from H, linear or branched C₁-C₈-alkyl,C₃-C₈-cycloalkyl, or form C₃-C₁₂-cycloalkyl together with the connectingC atom. Preferably, R₁ and R₂ are the same or different and areindependently selected from H or linear or branched C₁-C₈-alkyl.

For example, R₁ and R₂ are the same. In this embodiment, R₁ and R₂ arepreferably selected from H, linear or branched C₁-C₈-alkyl,C₃-C₈-cycloalkyl, linear or branched C₂-C₈-alkenyl, C₅-C₈-cycloalkenyl,linear or branched C₂-C₈-alkynyl, C₆-C₁₄-aryl or form C₃-C₁₂-cycloalkylor C₅-C₁₂-cycloalkenyl together with the connecting C atom.

In one embodiment, R₁ and R₂ are the same and are H.

In another embodiment, R₁ and R₂ are the same and are linear or branchedC₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl. For example, R₁ and R₂ are thesame and are linear or branched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl,preferably linear or branched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, andmost preferably linear or branched C₁-C₃-alkyl, e.g. linear C₁-C₃-alkyl.It is especially preferred that R₁ and R₂ are the same and are C₁- orC₂-alkyl, e.g. C₁-alkyl.

In another embodiment, R₁ and R₂ form C₃-C₁₂-cycloalkyl together withthe connecting C atom. For example, R₁ and R₂ form C₄-C₁₀-cycloalkyl,preferably C₄-C₈-cycloalkyl, more preferably C₄-C₆-cycloalkyl, and mostpreferably C₅- or C₆-cycloalkyl, e.g. C₆-cycloalkyl, together with theconnecting C atom.

In another embodiment, R₁ and R₂ are the same and are linear or branchedC₂-C₈-alkenyl, e.g. linear C₂-C₈-alkenyl. For example, R₁ and R₂ are thesame and are linear or branched C₂-C₆-alkenyl, e.g. linearC₂-C₆-alkenyl, preferably linear or branched C₂-C₄-alkenyl, e.g. linearC₂-C₄-alkenyl, and most preferably linear or branched C₂- or C₃-alkenyl,e.g. linear C₂- or C₃-alkenyl. It is especially preferred that R₁ and R₂are the same and are C₃-alkenyl.

In another embodiment, R₁ and R₂ are the same and are linear or branchedC₂-C₈-alkynyl, e.g. linear C₂-C₈-alkynyl. For example, R₁ and R₂ are thesame and are linear or branched C₂-C₆-alkynyl, e.g. linearC₂-C₆-alkynyl, preferably linear or branched C₂-C₄-alkynyl, e.g. linearC₂-C₄-alkynyl, and most preferably linear or branched C₂- or C₃-alkynyl,e.g. linear C₂- or C₃-alkynyl. It is especially preferred that R₁ and R₂are the same and are C₃-alkynyl.

In another embodiment, R₁ and R₂ are the same and are linear or branchedC₆-C₁₄-aryl, e.g. (unsubstituted) C₆-C₁₀-aryl or C₆-C₁₄-alkylaryl. Forexample, R₁ and R₂ are the same and are (unsubstituted) C₆- or C₁₀-aryl.Alternatively, R₁ and R₂ are the same and are C₈-C₁₂-alkylaryl.

In another embodiment, R₁ and R₂ form C₅-C₁₂-cycloalkenyl together withthe connecting C atom. For example, R₁ and R₂ form C₅-C₁₀-cycloalkenyl,preferably C₅-C₈-cycloalkenyl and most preferably C₅- orC₆-cycloalkenyl, e.g. C₆-cycloalkenyl, together with the connecting Catom.

If R₁ and R₂ are the same, it is preferred that R₁ and R₂ are linear orbranched C₁-C₈-alkyl, preferably linear C₁-C₈-alkyl, or formC₃-C₁₂-cycloalkyl, preferably C₅- or C₆-cycloalkyl, together with theconnecting C atom. More preferably, R₁ and R₂ are linear or branchedC₁-C₈-alkyl, preferably linear C₁-C₈-alkyl, or form C₃-C₁₂-cycloalkyl.Most preferably, R₁ and R₂ are linear or branched C₁-C₈-alkyl,preferably linear C₁-C₈-alkyl.

Alternatively, R₁ and R₂ are different. In this embodiment, R₁ and R₂are preferably independently selected from H, linear or branchedC₁-C₈-alkyl, C₃-C₈-cycloalkyl, linear or branched C₂-C₈-alkenyl,C₅-C₈-cycloalkenyl, linear or branched C₂-C₈-alkynyl or C₆-C₁₄-aryl. Forexample, R₁ and R₂ are different and are selected from H, linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, linear or branchedC₂-C₈-alkenyl, e.g. linear C₂-C₈-alkenyl, preferably linear or branchedC₂-C₆-alkenyl, e.g. linear C₂-C₆-alkenyl, more preferably linear orbranched C₂-C₄-alkenyl, e.g. linear C₂-C₄-alkenyl, even more preferablylinear or branched C₂- or C₃-alkenyl, e.g. linear C₂- or C₃-alkenyl andmost preferably C₃-alkenyl, and linear or branched C₂-C₈-alkynyl, e.g.linear C₂-C₈-alkynyl, preferably linear or branched C₂-C₆-alkynyl, e.g.linear C₂-C₆-alkynyl, more preferably linear or branched C₂-C₄-alkynyl,e.g. linear C₂-C₄-alkynyl, even more preferably linear or branched C₂-or C₃-alkynyl, e.g. linear C₂- or C₃-alkynyl and most preferablyC₃-alkynyl. In one embodiment, R₁ and R₂ are different and are selectedfrom H and linear or branched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl,preferably linear or branched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, morepreferably linear or branched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, andmost preferably linear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl. In oneembodiment, R₁ and R₂ are different and are selected from H and C₁- orC₂-alkyl, preferably C₂-alkyl.

If R₁ and R₂ are different, R₁ or R₂ is preferably H and the remainingR₁ or R₂ is preferably linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, even more preferably linear C₁-C₃-alkyl, and mostpreferably C₁- or C₂-alkyl, e.g. C₂-alkyl.

Preferably, R₁ and R₂ are the same.

The alkyl aryl ketone of the general formula I further comprisesresidues R₃, R₄, R₅, R₆ and R₇. It is appreciated that R₃, R₄, R₅, R₆and R₇ can be the same or different. Furthermore, R₃, R₄, R₅, R₆ and R₇are the same or different and are independently selected from H, linearor branched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl, C₁-C₈-alkoxy,C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl, C₆-C₁₄-aryl, C₃-C₈-cycloalkoxy,C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, N(R₈)₂ or SR₈ with R₈ beingselected from linear or branched C₁-C₈-alkyl, linear or branchedC₂-C₈-alkenyl, C₆-C₁₄-aryl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxy,C₉-C₁₅-alkenylarylalkoxy, or R₈ form a C₃-C₉-alicyclic system togetherwith the connecting N atom, or R₈ form a C₃-C₉-alicyclic system togetherwith the connecting N atom, optionally one or more carbon atoms arereplaced with O, or two adjacent R form an aromatic system together withthe benzene ring of formula I.

The term “C₁-C₈-alkoxy” in the meaning of the present invention meansthat the alkoxy moiety has a linear or branched chain alkyl having 1 to8 carbon atoms, and includes, for example, methoxy, ethoxy, propoxy,isopropoxy, butoxy, isobutoxy, tertiary butoxy, pentyloxy, hexyloxy,heptyloxy and octyloxy.

The term “C₂-C₈-alkenyloxy” in the meaning of the present inventionmeans that the alkenyloxy moiety has a linear or branched chain alkenylhaving 2 to 8 carbon atoms, and includes, for example, ethenyloxy,propenyloxy, butenyloxy, triisobutenyloxy, pentenyloxy, hexenyloxy,heptenyloxy and octenyloxy.

The term “C₃-C₈-cycloalkoxy” in the meaning of the present inventionmeans that the cycloalkoxy moiety has a cyclic alkyl having 3 to 8carbon atoms, and includes, for example, cyclopropyloxy, cyclobutyloxy,cyclopentyloxy, cyclohexyloxy, and cycloheptyloxy.

The term “C₇-C₁₅-arylalkoxy” in the meaning of the present inventionmeans that the alkoxy moiety has a linear or branched chain alkyl having1 to 4 carbon atoms, preferably 1 or 2 carbon atoms, which is connectedto C₆-C₁₄-aryl.

The term “C₇-C₁₅-arylalkyl” in the meaning of the present inventionmeans that the alkyl moiety is a linear or branched chain alkyl having 1to 4 carbon atoms, preferably 1 or 2 carbon atoms, which is connected toC₆-C₁₄-aryl.

The term “C₉-C₁₅-alkenylarylalkoxy” in the meaning of the presentinvention means that the alkoxy moiety has a linear or branched chainalkyl having 1 to 4 carbon atoms, preferably 1 or 2 carbon atoms, whichis connected to C₆-C₁₄-aryl, preferably C₆-aryl, which is furtherconnected to linear or branched C₂-C₈-alkenyl, preferably C₂-alkenyl.Preferably, the alkoxy and alkenyl moieties are connected inpara-position of the aryl moiety.

In one embodiment, R₃, R₄, R₅, R₆ and R₇ are the same. In thisembodiment, R₃, R₄, R₅, R₆ and R₇ are the same and are selected from Hand linear or branched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl. Forexample, R₃, R₄, R₅, R₆ and R₇ are the same and are linear or branchedC₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, preferably linear or branchedC₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferably linearC₁-C₃-alkyl, e.g. C₁- or C₂-alkyl. It is especially preferred that R₃,R₄, R₅, R₆ and R₇ are the same and are H.

Alternatively, R₃, R₄, R₅, R₆ and R₇ are different. In this embodiment,R₃, R₄, R₅, R₆ and R₇ are different and at least one of them is selectedfrom linear or branched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl,C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₉-C₁₅-alkenylarylalkoxy or N(R₈)₂ orSR₈ with R₈ being selected from linear or branched C₁-C₈-alkyl or linearor branched C₂-C₈-alkenyl or R₈ form a C₃-C₉-alicyclic system togetherwith the connecting N atom.

The term “at least one” in the meaning of the present invention meansthat one or more of R₃, R₄, R₅, R₆ and R₇ is selected from linear orbranched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl, C₁-C₈-alkoxy,C₂-C₈-alkenyloxy, C₉-C₁₅-alkenylarylalkoxy or N(R₈)₂ or SR₈ with R₈being selected from linear or branched C₁-C₈-alkyl or linear or branchedC₂-C₈-alkenyl or R₈ form a C₃-C₉-alicyclic system together with theconnecting N atom.

For example, one or two or three of R₃, R₄, R₅, R₆ and R₇ is/areselected from linear or branched C₁-C₈-alkyl, linear or branchedC₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₉-C₁₅-alkenylarylalkoxyor N(R₈)₂ or SR₈ with R₈ being selected from linear or branchedC₁-C₈-alkyl or linear or branched C₂-C₈-alkenyl or R₈ form aC₃-C₉-alicyclic system together with the connecting N atom. For example,one or two of R₃, R₄, R₅, R₆ and R₇ is/are selected from linear orbranched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl, C₁-C₈-alkoxy,C₂-C₈-alkenyloxy, C₉-C₁₅-alkenylarylalkoxy or N(R₈)₂ or SR₈ with R₈being selected from linear or branched C₁-C₈-alkyl or linear or branchedC₂-C₈-alkenyl or R₈ form a C₃-C₉-alicyclic system together with theconnecting N atom.

Preferably, one of R₃, R₄, R₅, R₆ and R₇ is selected from linear orbranched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl, C₁-C₈-alkoxy,C₂-C₈-alkenyloxy, C₉-C₁₅-alkenylarylalkoxy or N(R₈)₂ or SR₈ with R₈being selected from linear or branched C₁-C₈-alkyl or linear or branchedC₂-C₈-alkenyl or R₈ form a C₃-C₉-alicyclic system together with theconnecting N atom.

If R₃, R₄, R₅, R₆ and R₇ are different and at least one of them isselected from linear or branched C₁-C₈-alkyl, linear or branchedC₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₉-C₁₅-alkenylarylalkoxyor N(R₈)₂ or SR₈ with R₈ being selected from linear or branchedC₁-C₈-alkyl or linear or branched C₂-C₈-alkenyl or R₈ form aC₃-C₉-alicyclic system together with the connecting N atom, it ispreferred that the remaining ones are selected from H and linear orbranched C₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, morepreferably linear or branched C₁-C₄-alkyl and most preferably linearC₁-C₃-alkyl, e.g. C₁- or C₂-alkyl. For example, R₃, R₄, R₅, R₆ and R₇are different and at least one of them is selected from linear orbranched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl, C₁-C₈-alkoxy,C₂-C₈-alkenyloxy, C₉-C₁₅-alkenylarylalkoxy or N(R₈)₂ or SR₈ with R₈being selected from linear or branched C₁-C₈-alkyl or linear or branchedC₂-C₈-alkenyl or R₈ form a C₃-C₉-alicyclic system together with theconnecting N atom and the remaining ones are H.

In one embodiment, R₃, R₄, R₅, R₆ and R₇ are different and one of themis selected from linear or branched C₁-C₈-alkyl, linear or branchedC₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₉-C₁₅-alkenylarylalkoxyor N(R₈)₂ or SR₈ with R₈ being selected from linear or branchedC₁-C₈-alkyl or linear or branched C₂-C₈-alkenyl or R₈ form aC₃-C₉-alicyclic system together with the connecting N atom.

For example, R₃, R₄, R₅, R₆ and R₇ are different and one of them islinear or branched C₂-C₈-alkenyl, e.g. linear C₂-C₈-alkenyl; preferablylinear or branched C₂-C₆-alkenyl, e.g. linear C₂-C₆-alkenyl; and mostpreferably C₂-C₃-alkenyl, e.g. C₂- or C₃-alkenyl; and the remaining onesare H.

Alternatively, R₃, R₄, R₅, R₆ and R₇ are different and one of them isC₂-C₈-alkenyloxy, preferably C₂-C₆-alkenyloxy and most preferablyC₃-C₅-alkenyloxy, e.g. C₃- or C₄-alkenyloxy, especially C₃-alkenyloxy;and the remaining ones are H.

In one embodiment, R₃, R₄, R₅, R₆ and R₇ are different and one of themis C₂-C₈-alkenyloxy, preferably C₂-C₆-alkenyloxy and most preferablyC₃-C₅-alkenyloxy, e.g. C₃- or C₄-alkenyloxy, especially C₃-alkenyloxy;and the remaining ones are independently selected from H and linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl.

For example, R₃, R₄, R₅, R₆ and R₇ are different and one of them isC₂-C₈-alkenyloxy, preferably C₂-C₆-alkenyloxy and most preferablyC₃-C₅-alkenyloxy, e.g. C₃- or C₄-alkenyloxy, especially C₃-alkenyloxy;and two of the remaining ones are H and two of the remaining ones arelinear or branched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferablylinear or branched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferablylinear or branched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and mostpreferably linear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especiallyC₁-alkyl.

Alternatively, R₃, R₄, R₅, R₆ and R₇ are different and one of them isC₉-C₁₅-alkenylarylalkoxy, preferably C₉-C₁₂-alkenylarylalkoxy and mostpreferably C₉-C₁₀-alkenylarylalkoxy; and the remaining ones are H.

Alternatively, R₃, R₄, R₅, R₆ and R₇ are different and one of them isSR₈ with R₈ being selected from linear or branched C₁-C₈-alkyl, e.g.linear C₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g.linear C₁-C₆-alkyl, preferably linear or branched C₁-C₄-alkyl, e.g.linear C₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl; and the remaining ones are H.

Alternatively, R₃, R₄, R₅, R₆ and R₇ are different and one of them isN(R₈)₂ with R₈ forming a C₃-C₉-alicyclic system, preferably aC₃-C₇-alicyclic system, more preferably a C₄-C₆-alicyclic system andmost preferably a C₅- or C₆-alicyclic system, together with theconnecting N atom; and the remaining ones are H. Optionally one or morecarbon atoms are replaced with O. Preferably, R₃, R₄, R₅, R₆ and R₇ aredifferent and one of them is N(R₈)₂ with R₈ forming a C₃-C₉-alicyclicsystem, preferably a C₃-C₇-alicyclic system, more preferably aC₄-C₆-alicyclic system and most preferably a C₅- or C₆-alicyclic system,together with the connecting N atom, wherein one or more, preferablyone, carbon atoms are replaced with O; and the remaining ones are H.

If R₃, R₄, R₅, R₆ and R₇ are different and one of them is selected fromlinear or branched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl,C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₉-C₁₅-alkenylarylalkoxy or N(R₈)₂ orSR₈ with R₈ being selected from linear or branched C₁-C₈-alkyl or linearor branched C₂-C₈-alkenyl or R₈ form a C₃-C₉-alicyclic system togetherwith the connecting N atom, it is preferred that R₅ is selected fromlinear or branched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl,C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₉-C₁₅-alkenylarylalkoxy or N(R₈)₂ orSR₈ with R₈ being selected from linear or branched C₁-C₈-alkyl or linearor branched C₂-C₈-alkenyl or R₈ form a C₃-C₉-alicyclic system togetherwith the connecting N atom.

Thus, if R₃, R₄, R₅, R₆ and R₇ are different and one of them is selectedfrom linear or branched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl,C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₉-C₁₅-alkenylarylalkoxy or N(R₈)₂ orSR₈ with R₈ being selected from linear or branched C₁-C₈-alkyl or linearor branched C₂-C₈-alkenyl or R₈ form a C₃-C₉-alicyclic system togetherwith the connecting N atom, it is preferred that this group is inpara-position to the keto group.

In an alternative embodiment, R₃, R₄, R₅, R₆ and R₇ are different andtwo or three of them are linear or branched C₂-C₈-alkenyl, e.g. linearC₂-C₈-alkenyl, preferably linear or branched C₂-C₆-alkenyl, e.g. linearC₂-C₆-alkenyl, and most preferably C₂-C₃-alkenyl; C₁-C₈-alkoxy,preferably C₁-C₆-alkoxy and most preferably C₁-C₃-alkoxy;C₂-C₈-alkenyloxy, preferably C₂-C₆-alkenyloxy and most preferablyC₃-C₅-alkenyloxy; and C₉-C₁₅-alkenylarylalkoxy, preferablyC₉-C₁₂-alkenylarylalkoxy and most preferably C₉-C₁₀-alkenylarylalkoxy,and the remaining ones are independently selected from H and linear orbranched C₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, morepreferably linear or branched C₁-C₄-alkyl and most preferably linearC₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl.

For example, R₃, R₄, R₅, R₆ and R₇ are different and two of them arelinear or branched C₂-C₈-alkenyl, e.g. linear C₂-C₈-alkenyl, preferablylinear or branched C₂-C₆-alkenyl, e.g. linear C₂-C₆-alkenyl, and mostpreferably C₂-C₃-alkenyl; C₁-C₈-alkoxy, preferably C₁-C₆-alkyloxy andmost preferably C₁-C₃-alkyloxy; C₂-C₈-alkenyloxy, preferablyC₂-C₆-alkenyloxy and most preferably C₃-C₅-alkenyloxy; andC₉-C₁₅-alkenylarylalkoxy, preferably C₉-C₁₂-alkenylarylalkoxy and mostpreferably C₉-C₁₀-alkenylarylalkoxy, and the remaining ones areindependently selected from H and linear or branched C₁-C₈-alkyl,preferably linear or branched C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl. Preferably, R₃, R₄, R₅, R₆ and R₇ aredifferent and two of them are C₂-C₈-alkenyloxy, preferablyC₂-C₆-alkenyloxy and most preferably C₃-C₅-alkenyloxy; and the remainingones are independently selected from H and linear or branchedC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, more preferablylinear or branched C₁-C₄-alkyl and most preferably linear C₁-C₃-alkyl,e.g. C₁- or C₂-alkyl, especially C₁-alkyl, preferably the remaining onesare H.

Alternatively, R₃, R₄, R₅, R₆ and R₇ are different and two of them areC₁-C₈-alkoxy, preferably C₁-C₆-alkoxy and most preferably C₁-C₃-alkoxy;and the remaining ones are independently selected from H and linear orbranched C₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, morepreferably linear or branched C₁-C₄-alkyl and most preferably linearC₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl, preferably theremaining ones are H.

In one embodiment, R₃, R₄, R₅, R₆ and R₇ are different and three of themare C₉-C₁₅-alkenylarylalkoxy, preferably C₉-C₁₂-alkenylarylalkoxy andmost preferably C₉-C₁₀-alkenylarylalkoxy, and the remaining ones areindependently selected from H and linear or branched C₁-C₈-alkyl,preferably linear or branched C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl, preferably the remaining ones are H.

If two or three of R₃, R₄, R₅, R₆ and R₇ are linear or branchedC₂-C₈-alkenyl, e.g. linear C₂-C₈-alkenyl, preferably linear or branchedC₂-C₆-alkenyl, e.g. linear C₂-C₆-alkenyl, and most preferablyC₂-C₃-alkenyl; C₁-C₈-alkoxy, preferably C₁-C₆-alkyloxy and mostpreferably C₁-C₃-alkyloxy; C₂-C₈-alkenyloxy, preferably C₂-C₆-alkenyloxyand most preferably C₃-C₅-alkenyloxy; and C₉-C₁₅-alkenylarylalkoxy,preferably C₉-C₁₂-alkenylarylalkoxy and most preferablyC₉-C₁₀-alkenylarylalkoxy, it is appreciated that preferably R₄ and/or R₅and/or R₆ are linear or branched C₂-C₈-alkenyl, e.g. linearC₂-C₈-alkenyl, preferably linear or branched C₂-C₆-alkenyl, e.g. linearC₂-C₆-alkenyl, and most preferably C₂-C₃-alkenyl; C₁-C₈-alkoxy,preferably C₁-C₆-alkyloxy and most preferably C₁-C₃-alkyloxy;C₂-C₈-alkenyloxy, preferably C₂-C₆-alkenyloxy and most preferablyC₃-C₅-alkenyloxy; and C₉-C₁₅-alkenylarylalkoxy, preferablyC₉-C₁₂-alkenylarylalkoxy and most preferably C₉-C₁₀-alkenylarylalkoxy.

In one embodiment, R₃ and R₄ or R₄ and R₅ form an aromatic systemtogether with the benzene ring of general formula I, preferably abicyclic, tricyclic or tetracyclic aromatic system, more preferably anaromatic system selected from a naphthyl, anthracenyl and phenanthrenylsystem. The aromatic system is preferably a bicyclic aromatic system,most preferably naphthyl.

For example, R₄ and R₅ form an aromatic system together with the benzenering of general formula I, preferably a bicyclic aromatic system, mostpreferably naphthyl; and the remaining ones are independently selectedfrom H and linear or branched C₁-C₈-alkyl, preferably linear or branchedC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl and mostpreferably linear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especiallyC₁-alkyl, preferably H.

It is appreciated that one of the remaining R may be linear or branchedC₂-C₈-alkenyl, preferably C₂-C₆-alkenyl and most preferablyC₂-C₃-alkenyl; C₂-C₈-alkenyloxy, preferably C₂-C₆-alkenyloxy and mostpreferably C₃-C₅-alkenyloxy; and C₉-C₁₅-alkenylarylalkoxy, preferablyC₉-C₁₂-alkenylarylalkoxy and most preferably C₉-C₁₀-alkenylarylalkoxy;and the remaining ones may be independently selected from H and linearor branched C₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, morepreferably linear or branched C₁-C₄-alkyl and most preferably linearC₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl, preferably H.

In one embodiment, R₄ and R₅ form an aromatic system together with thebenzene ring of general formula I, preferably a bicyclic aromaticsystem, most preferably naphthyl, and R₃ is linear or branchedC₂-C₈-alkenyl, preferably C₂-C₆-alkenyl and most preferablyC₂-C₃-alkenyl; C₂-C₈-alkenyloxy, preferably C₂-C₆-alkenyloxy and mostpreferably C₃-C₅-alkenyloxy; and C₉-C₁₅-alkenylarylalkoxy, preferablyC₉-C₁₂-alkenylarylalkoxy and most preferably C₉-C₁₀-alkenylarylalkoxy;and the remaining ones are independently selected from H and linear orbranched C₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, morepreferably linear or branched C₁-C₄-alkyl and most preferably linearC₁-C₃-alkyl, preferably H. For example, R₄ and R₅ form an aromaticsystem together with the benzene ring of general formula I, preferably abicyclic aromatic system, most preferably naphthyl, and R₃ isC₉-C₁₅-alkenylarylalkoxy, preferably C₉-C₁₂-alkenylarylalkoxy and mostpreferably C₉-C₁₀-alkenylarylalkoxy; and the remaining ones are H.

An especially preferred alkyl aryl ketone of the general formula I is aketone, wherein R₁ and R₂ are the same and are selected from linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl; and R₃,R₄, R₅, R₆ and R₇ are the same and are H.

For example, the alkyl aryl ketone of the general formula I is a ketone,wherein R₁ and R₂ are the same and are C₁-alkyl; and R₃, R₄, R₅, R₆ andR₇ are the same and are H.

Alternatively, the alkyl aryl ketone of the general formula I is aketone, wherein R₁ and R₂ form C₃-C₁₂-cycloalkyl, preferablyC₄-C₁₀-cycloalkyl, more preferably C₄-C₈-cycloalkyl, even morepreferably C₄-C₆-cycloalkyl, and most preferably C₅- or C₆-cycloalkyl,e.g. C₆-cycloalkyl, together with the connecting C atom; and R₄, R₅, R₆and R₇ are the same and are H.

Alternatively, the alkyl aryl ketone of the general formula I is aketone, wherein R₁ and R₂ are the same and are selected from linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl; and R₄,R₅, R₆ and R₇ are the same and are H.

Alternatively, the alkyl aryl ketone of the general formula I is aketone, wherein R₁ and R₂ are the same and are selected from linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl; R₄, R₅,R₆ and R₇ are different and one of them, preferably R₅, is linear orbranched C₂-C₈-alkenyl, preferably linear or branched C₂-C₆-alkenyl andmost preferably C₂-C₃-alkenyl, e.g. C₂-alkenyl; and the remaining onesare H.

For example, the alkyl aryl ketone of the general formula I is a ketone,wherein R₁ and R₂ are the same and are C₁-alkyl; R₄, R₅, R₆ and R₇ aredifferent and one of them, preferably R₅, is linear or branchedC₂-C₈-alkenyl, preferably linear or branched C₂-C₆-alkenyl and mostpreferably C₂-C₃-alkenyl, e.g. C₂-alkenyl; and the remaining ones are H.

Alternatively, the alkyl aryl ketone of the general formula I is aketone, wherein R₁ and R₂ are the same and are selected from linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl; R₄, R₅,R₆ and R₇ are different and one of them, preferably R₅, is linear orbranched C₂-C₈-alkenyl, preferably linear or branched C₂-C₆-alkenyl andmost preferably C₂-C₃-alkenyl, e.g. C₂-alkenyl; and the remaining onesare H.

For example, the alkyl aryl ketone of the general formula I is a ketone,wherein R₁ and R₂ are the same and are C₁-alkyl; R₄, R₅, R₆ and R₇ aredifferent and one of them, preferably R₅, is linear or branchedC₂-C₈-alkenyl, preferably linear or branched C₂-C₆-alkenyl and mostpreferably C₂-C₃-alkenyl, e.g. C₂-alkenyl; and the remaining ones are H.

Alternatively, the alkyl aryl ketone of the general formula I is aketone, wherein R₁ and R₂ are the same and are selected from linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferably Ilinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl; R₄, R₅,R₆ and R₇ are different and one of them, preferably R₅, is SR₈ with R₈being selected from linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear or branched C₁-C₃-alkyl, e.g.linear C₁- or C₃-alkyl, especially C₁-alkyl; and the remaining ones areH.

For example, the alkyl aryl ketone of the general formula I is a ketone,wherein R₁ and R₂ are the same and are C₁-alkyl; R₄, R₅, R₆ and R₇ aredifferent and one of them, preferably R₅, is SR₈ with R₈ being selectedfrom linear or branched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferablylinear or branched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferablylinear or branched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and mostpreferably linear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especiallyC₁-alkyl; and the remaining ones are H.

Alternatively, the alkyl aryl ketone of the general formula I is aketone, wherein R₁ and R₂ are the same and are selected from linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl; R₄, R₅,R₆ and R₇ are different and one of them, preferably R₅, is SR₈ with R₈being selected from linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl; and the remaining ones are H.

For example, the alkyl aryl ketone of the general formula I is a ketone,wherein R₁ and R₂ are the same and are C₁-alkyl; R₄, R₅, R₆ and R₇ aredifferent and one of them, preferably R₅, is SR₈ with R₈ being selectedfrom linear or branched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferablylinear or branched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferablylinear or branched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and mostpreferably linear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especiallyC₁-alkyl; and the remaining ones are H.

Alternatively, the alkyl aryl ketone of the general formula I is aketone, wherein R₁ and R₂ are the same and are selected from linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl; R₃, R₄,R₅, R₆ and R₇ are different and one of them is C₂-C₈-alkenyloxy,preferably C₂-C₆-alkenyloxy and most preferably C₃-C₅-alkenyloxy, e.g.C₃- or C₄-alkenyloxy, especially C₃-alkenyloxy; and two of the remainingones are H and two of the remaining ones are linear or branchedC₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear or branchedC₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear or branchedC₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferably linearC₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl.

For example, the alkyl aryl ketone of the general formula I is a ketone,wherein R₁ and R₂ are the same and are C₁-alkyl; R₃, R₄, R₅, R₆ and R₇are different and one of them, preferably R₅, is C₂-C₈-alkenyloxy,preferably C₂-C₆-alkenyloxy and most preferably C₃-C₅-alkenyloxy, e.g.C₃- or C₄-alkenyloxy, especially C₃-alkenyloxy; and two of the remainingones, preferably R₃ and R₇, are H and two of the remaining ones,preferably R₄ and R₆, are linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl.

Alternatively, the alkyl aryl ketone of the general formula I is aketone, wherein R₁ and R₂ are the same and are selected from linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl; R₃, R₄,R₅, R₆ and R₇ are different and three of them, preferably R₃ and R₄ andR₅, are C₉-C₁₅-alkenylarylalkoxy, preferably C₉-C₁₂-alkenylarylalkoxyand most preferably C₉-C₁₀-alkenylarylalkoxy, and the remaining ones,preferably R₆ and R₇ are H.

For example, the alkyl aryl ketone of the general formula I is a ketone,wherein R₁ and R₂ are the same and are C₁-alkyl; R₃, R₄, R₅, R₆ and R₇are different and three of them, preferably R₃ and R₄ and R₅, areC₉-C₁₅-alkenylarylalkoxy, preferably C₉-C₁₂-alkenylarylalkoxy and mostpreferably C₉-C₁₀-alkenylarylalkoxy, and the remaining ones, preferablyR₆ and R₇ are H.

Alternatively, the alkyl aryl ketone of the general formula I is aketone, wherein R₁ and R₂ are different and are selected from H andlinear or branched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferablylinear or branched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferablylinear or branched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and mostpreferably linear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especiallyC₁-alkyl; R₃, R₄, R₅, R₆ and R₇ are different and two of them,preferably R₄ and R₅, are C₁-C₈-alkoxy, preferably C₁-C₆-alkoxy and mostpreferably C₁-C₃-alkoxy, especially C₁-alkoxy; and the remaining ones,preferably R₃, R₆ and R₇, are H.

For example, the alkyl aryl ketone of the general formula I of thegeneral formula I is a ketone, wherein R₁ and R₂ are different and are Hand C₂-alkyl; R₃, R₄, R₅, R₆ and R₇ are different and two of them,preferably R₄ and R₅, are C₁-C₈-alkoxy, preferably C₁-C₆-alkoxy and mostpreferably C₁-C₃-alkoxy, especially C₁-alkoxy; and the remaining ones,preferably R₃, R₆ and R₇, are H.

Alternatively, the alkyl aryl ketone of the general formula I is aketone, wherein R₁ and R₂ are different and are selected from H andlinear or branched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferablylinear or branched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferablylinear or branched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and mostpreferably linear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especiallyC₁-alkyl; R₃, R₄, R₅, R₆ and R₇ are different and one of them,preferably R₅, is N(R₈)₂ with R₈ forming a C₃-C₉-alicyclic system,preferably a C₃-C₇-alicyclic system, more preferably a C₄-C₆-alicyclicsystem and most preferably a C₅- or C₆-alicyclic system, together withthe connecting N atom, wherein one or more, preferably one, carbon atomsare replaced with O; and the remaining ones, preferably R₃, R₄, R₆ andR₇, are H.

For example, the alkyl aryl ketone of the general formula I is a ketone,wherein R₁ and R₂ are different and are H and C₂-alkyl; R₃, R₄, R₅, R₆and R₇ are different and one of them, preferably R₅, is N(R₈)₂ with R₈forming a C₃-C₉-alicyclic system, preferably a C₃-C₇-alicyclic system,more preferably a C₄-C₆-alicyclic system and most preferably a C₅- orC₆-alicyclic system, together with the connecting N atom, wherein one ormore, preferably one, carbon atoms are replaced with O; and theremaining ones, preferably R₃, R₄, R₆ and R₇, are H.

Alternatively, the alkyl aryl ketone of the general formula I is aketone, wherein R₁ and R₂ are the same and are selected from linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl; R₄ and R₅form an aromatic system together with the benzene ring of generalformula I, preferably a bicyclic aromatic system, most preferablynaphthyl; and the remaining ones are independently selected from H andlinear or branched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferablylinear or branched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferablylinear or branched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and mostpreferably linear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especiallyC₁-alkyl, preferably H.

For example, the alkyl aryl ketone of the general formula I is a ketone,wherein R₁ and R₂ are the same and are C₁-alkyl; R₄ and R₅ form anaromatic system together with the benzene ring of general formula I,preferably a bicyclic aromatic system, most preferably naphthyl; and theremaining ones are H.

Alternatively, the alkyl aryl ketone of the general formula I is aketone, wherein R₁ and R₂ are the same and are selected from linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl; R₄ and R₅form an aromatic system together with the benzene ring of generalformula I, preferably a bicyclic aromatic system, most preferablynaphthyl; and one of the remaining R, preferably R₃, is linear orbranched C₂-C₈-alkenyl, preferably C₂-C₆-alkenyl and most preferablyC₂-C₃-alkenyl; C₂-C₈-alkenyloxy, preferably C₂-C₆-alkenyloxy and mostpreferably C₃-C₅-alkenyloxy; and C₉-C₁₅-alkenylarylalkoxy, preferablyC₉-C₁₂-alkenylarylalkoxy and most preferably C₉-C₁₀-alkenylarylalkoxyand the remaining ones are H.

For example, the alkyl aryl ketone of the general formula I is a ketone,wherein R₁ and R₂ are the same and are C₁-alkyl; R₄ and R₅ form anaromatic system together with the benzene ring of general formula I,preferably a bicyclic aromatic system, most preferably naphthyl; and oneof the remaining R, preferably R₃, is C₉-C₁₅-alkenylarylalkoxy,preferably C₉-C₁₂-alkenylarylalkoxy and most preferablyC₉-C₁₀-alkenylarylalkoxy and the remaining ones are H.

It is appreciated that the alkyl aryl ketone of the general formula I isreacted with an at least partially halogenated C₂-C₈-alkane and/orC₂-C₈-alkene, and a base selected from alkali metal C₁-C₈-alkoxide,earth alkali metal C₁-C₈-alkoxide and mixtures thereof, obtainingthereby the corresponding aryl oxirane or α-functionalized alkyl arylketal.

It is preferred that the at least partially halogenated C₂-C₈-alkaneand/or C₂-C₈-alkene is an at least partially halogenated C₂-C₆-alkaneand/or C₂-C₆-alkene, more preferably an at least partially halogenatedC₂-C₄-alkane and/or C₂-C₄-alkene. For example, the at least partiallyhalogenated C₂-C₈-alkane and/or C₂-C₈-alkene is an at least partiallyhalogenated C₂- or C₃-alkane and/or C₂- or C₃-alkene, e.g. an at leastpartially halogenated C₂-alkane and/or C₂-alkene.

The at least partially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene maybe at least partially chlorinated and/or brominated. For example, the atleast partially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene is at leastpartially chlorinated or brominated. Alternatively, the at leastpartially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene is at leastpartially chlorinated and brominated, and thus is a mixed halogenatedC₂-C₈-alkane and/or C₂-C₈-alkene.

Preferably, the at least partially halogenated C₂-C₈-alkane and/orC₂-C₈-alkene is at least partially chlorinated.

In one embodiment, the at least partially halogenated C₂-C₈-alkaneand/or C₂-C₈-alkene is fully halogenated. Preferably, the at leastpartially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene is a fullyhalogenated C₂-C₆-alkane and/or C₂-C₆-alkene, more preferably a fullyhalogenated C₂-C₄-alkane and/or C₂-C₄-alkene. For example, the at leastpartially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene is a fullyhalogenated C₂- or C₃-alkane and/or C₂- or C₃-alkene.

For example, the at least partially halogenated C₂-C₈-alkane and/orC₂-C₈-alkene may be fully chlorinated and/or brominated. For example,the at least partially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene isfully chlorinated or brominated. Alternatively, the at least partiallyhalogenated C₂-C₈-alkane and/or C₂-C₈-alkene is fully chlorinated andbrominated, and thus is a mixed halogenated C₂-C₈-alkane and/orC₂-C₈-alkene.

Preferably, the at least partially halogenated C₂-C₈-alkane and/orC₂-C₈-alkene is fully chlorinated.

In one embodiment, the at least partially halogenated C₂-C₈-alkaneand/or C₂-C₈-alkene is selected from hexachloroethane,tetrachoroethylene, pentachloropropane, hexabromoethane,tetrabromoethylene, pentabromopropane and mixtures thereof. Preferably,the at least partially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene ishexachloroethane, tetrachoroethylene and mixtures thereof. For example,the at least partially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene ishexachloroethane or tetrachoroethylene.

In one embodiment, the at least partially halogenated C₂-C₈-alkaneand/or C₂-C₈-alkene is hexachloroethane.

Another requirement of the process is the addition of a base. It is arequirement of the present invention that the base is selected from thegroup comprising alkali metal C₁-C₈-alkoxide, earth alkali metalC₁-C₈-alkoxide and mixtures thereof.

In one embodiment, the base is selected from the group comprising sodiumC₁-C₆-alkoxide, preferably sodium C₁-C₄-alkoxide and most preferablysodium C₁-C₂-alkoxide; lithium C₁-C₆-alkoxide, preferably lithiumC₁-C₄-alkoxide and most preferably lithium C₁-C₂-alkoxide; potassiumC₁-C₆-alkoxide, preferably potassium C₁-C₄-alkoxide and most preferablypotassium C₁-C₂-alkoxide; and mixtures thereof. Preferably, the base issodium C₁-C₆-alkoxide, preferably sodium C₁-C₄-alkoxide and mostpreferably sodium C₁-C₂-alkoxide. Most preferably, the base is sodiumC₁-alkoxide.

The base can be added as such into the process. Alternatively, the baseis in form of an aqueous solution or the base is provided in an organicsolvent, preferably the organic solvent is selected from the groupcomprising methanol, ethanol, n-propanol, tert.-butanol,dichloromethane, tetrachloroethylene, tetrahydrofuran, ethyl acetate,acetone, N,N-dimethylformamide, dimethyl sulfoxide and mixtures thereof.Preferably, the base is provided in an organic solvent, preferably theorganic solvent is methanol.

The process of the present invention can be carried out over a widetemperature range. For example, the process is carried out at atemperature in the range from 0 to 120° C., preferably in the range from12 to 80° C., more preferably in the range from to 50° C., and mostpreferably in the range from 15 to 30° C.

Preferably, the process is carried out at room temperature, i.e. at atemperature of about 21° C. (±2° C.).

In one embodiment, it is preferred that the process is carried out atelevated temperature. That is to say, the process is carried out at atemperature above room temperature, preferably in the range from 30 to120° C., more preferably in the range from 40 to 100° C., and mostpreferably in the range from 40 to 90° C.

It is further appreciated that the process can be carried out in anorganic solvent. Preferably the organic solvent is selected from thegroup comprising methanol, ethanol, n-propanol, tert.-butanol,dichloromethane, tetrachloroethylene, tetrahydrofuran, ethyl acetate,acetone, N,N-dimethylformamide, dimethyl sulfoxide, dioxane such as1,3-dioxane or 1,4-dioxane, 1,2-dimethoxyethane, diethyleneglycoldimethyl ether, triethyleneglycol dimethyl ether and mixtures thereof.

If the base is provided in an organic solvent, the organic solvent ispreferably the same as used in the process. Thus, the organic solvent ispreferably methanol.

The reaction and contacting are carried out by mixing the components,i.e. the alkyl aryl ketone of the general formula I, the at leastpartially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene, and the baseselected from alkali metal C₁-C₈-alkoxide, earth alkali metalC₁-C₈-alkoxide and mixtures thereof. The skilled man will adapt themixing conditions (such as the configuration of mixing tools and mixingspeed) according to his process equipment.

It has been found that the sequence of addition of the reagents isunimportant for the success of the reaction. Thus, the alkyl aryl ketoneof the general formula I, the base selected from alkali metalC₁-C₈-alkoxide, earth alkali metal C₁-C₈-alkoxide and mixtures thereof,the at least partially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene and,if present, the organic solvent, can be contacted in any order.

Preferably, the alkyl aryl ketone of the general formula I, the baseselected from alkali metal C₁-C₈-alkoxide, earth alkali metalC₁-C₈-alkoxide and mixtures thereof, and, if present, the organicsolvent are contacted first and the at least partially halogenatedC₂-C₈-alkane and/or C₂-C₈-alkene is metered in.

It is appreciated that the process for reacting the alkyl aryl ketone ofthe general formula I, with the at least partially halogenatedC₂-C₈-alkane and/or C₂-C₈-alkene, and a base selected from alkali metalC₁-C₈-alkoxide, earth alkali metal C₁-C₈-alkoxide and mixtures thereof,results in the corresponding aryl oxirane or α-functionalized alkyl arylketal. The obtained aryl oxirane is preferably of the following generalformula Ia.

With regard to the definition of R₁, R₂, R₃, R₄, R₅, R₆, and R₇ andpreferred embodiments thereof, reference is made to the statementsprovided above when discussing the technical details of the process andthe alkyl aryl ketone of the general formula I used as starting materialin the process of the present invention.

The obtained α-functionalized alkyl aryl ketal is preferably of thefollowing general formula Ib.

With regard to the definition of R₁, R₂, R₃, R₄, R₅, R₆, and R₇ andpreferred embodiments thereof, reference is made to the statementsprovided above when discussing the technical details of the process andthe alkyl aryl ketone of the general formula I used as starting materialin the process of the present invention.

The process of the present invention may comprise further steps forisolating and/or purifying the obtained aryl oxirane or α-functionalizedalkyl aryl ketal.

For example, the process may further comprise a step of

-   -   i) separating the obtained aryl oxirane or α-functionalized        alkyl aryl ketal from the organic phase, and/or    -   ii) taking up the obtained aryl oxirane or α-functionalized        alkyl aryl ketal in water and extracting the obtained aqueous        phase with an organic solvent.

In one embodiment, the process further comprises the steps of

-   -   i) separating the obtained aryl oxirane or α-functionalized        alkyl aryl ketal from the organic phase, and    -   ii) taking up the obtained aryl oxirane or α-functionalized        alkyl aryl ketal in water and extracting the obtained aqueous        phase with an organic solvent.

Additionally, the process may further comprise a step of drying theobtained aryl oxirane or α-functionalized alkyl aryl ketal.

It is appreciated that the aryl oxirane or α-functionalized alkyl arylketal obtained by the process can be further reacted to thecorresponding α-functionalized ketone.

In one embodiment, the process of the present invention thus comprises afurther step of contacting the aryl oxirane obtained by the processunder phase-transfer conditions with a base selected from the groupcomprising alkali metal hydroxide, earth alkali metal hydroxide, alkalimetal C₁-C₈-alkoxide, earth alkali metal C₁-C₈-alkoxide and mixtures andthe a compound selected from HOR₉, HNHR₉ or HNR₁₀R₁₁ with R₉, R₁₀ andR₁₁ being independently selected from H, linear or branched C₁-C₈-alkyl,linear or branched C₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy, C₆-C₁₄-aryl, C₇-C₁₅-arylalkyl,C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, C₉-C₁₅-alkenylarylalkyl; orR₁₀ and R₁₁ form a C₃-C₉-alicyclic system together with the connecting Nor C atom, optionally one or more carbon atoms are replaced with O,resulting thereby in the corresponding α-functionalized ketone.

If an α-functionalized ketone is to be prepared from the aryl oxirane,it is thus required that the process is carried out under phase-transferconditions. Such phase-transfer conditions are well known in the artsuch that the skilled person will easily apply reaction conditions thatare suitable for the reaction mentioned. The skilled person can alsoapply variants of such reactions which are known per se and are notmentioned herein in detail.

In particular, the reaction of the aryl oxirane is carried out in thepresence of a phase-transfer catalyst with the base selected from thegroup comprising alkali metal hydroxide, earth alkali metal hydroxide,alkali metal C₁-C₈-alkoxide, earth alkali metal C₁-C₈-alkoxide andmixtures and the compound selected from HOR₉, HNHR₉ or HNR₁₀R₁₁ with R₉,R₁₀ and R₁₁ being independently selected from H, linear or branchedC₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl, C₁-C₈-alkoxy,C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy, C₆-C₁₄-aryl,C₇-C₁₅-arylalkyl, C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy,C₉-C₁₅-alkenylarylalkyl; or R₁₀ and R₁₁ form a C₃-C₉-alicyclic systemtogether with the connecting N or C atom, optionally one or more carbonatoms are replaced with O.

The phase-transfer catalyst can be selected from any phase-transfercatalyst known in the art. However, the phase-transfer catalyst ispreferably selected from a quaternary ammonium salt,tetraalkylphosphonium chloride, tetraalkylphosphonium bromide andmixtures thereof. More preferably, the phase-transfer catalyst is atetraalkylammonium salt or a trialkylarylammonium salt, and mostpreferably the phase-transfer catalyst is selected from the groupcomprising benzyltrimethylammonium hydroxide, benzyltriethylammoniumchloride, tetrabutylammonium chloride, tetrabutylammonium bromide,tetrabutylammonium hydrogensulfate, tetrabutylammonium hydroxide,methyltrioctylammonium chloride, cetyl pyridinium and mixtures thereof

Such phase-transfer catalysts are well known in the art such that theskilled person will easily apply catalysts that are suitable for thereaction mentioned. The skilled person can also apply variants of suchcatalysts which are known per se and are not mentioned herein in detail.

The amount of phase-transfer catalysts can be chosen as desired withinwide limits, preferably being 0.1 to 100 wt.-%, based on the weight ofthe aryl oxirane.

It is preferred that the base is selected from the group comprisingsodium hydroxide; potassium hydroxide; sodium C₁-C₆-alkoxide, preferablysodium C₁-C₄-alkoxide and most preferably sodium C₁-C₂-alkoxide; lithiumC₁-C₆-alkoxide, preferably lithium C₁-C₄-alkoxide and most preferablylithium C₁-C₂-alkoxide; potassium C₁-C₆-alkoxide, preferably potassiumC₁-C₄-alkoxide and most preferably potassium C₁-C₂-alkoxide; andmixtures thereof. Preferably, the base is selected from the groupcomprising sodium hydroxide and sodium C₁-C₆-alkoxide, preferably sodiumC₁-C₄-alkoxide and most preferably sodium C₁-C₂-alkoxide. Mostpreferably, the base is sodium hydroxide.

The base can be added as such into the process. Alternatively, the baseis in form of an aqueous solution or the base is provided in an organicsolvent, preferably the organic solvent is selected from the groupcomprising methanol, ethanol, n-propanol, tert.-butanol,dichloromethane, tetrachloroethylene, tetrahydrofuran, ethyl acetate,acetone, N,N-dimethylformamide, dimethyl sulfoxide, dioxane, such as1,3-dioxane or 1,4-dioxane, 1,2-dimethoxyethane, diethyleneglycoldimethyl ether, triethyleneglycol dimethyl ether and mixtures thereof.Preferably, the base is provided in form of an aqueous solution.

Another essential component to be added for reacting the obtained aryloxirane to the corresponding α-functionalized ketone, is a compoundselected from HOR₉, HNHR₉ or HNR₁₀R₁₁ with R₉, R₁₀ and R₁₁ beingindependently selected from H, linear or branched C₁-C₈-alkyl, linear orbranched C₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy, C₆-C₁₄-aryl, C₇-C₁₄-arylalkyl,C₇-C₁₄-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, C₉-C₁₅-alkenylarylalkyl; orR₁₀ and R₁₁ form a C₃-C₉-alicyclic system together with the connecting Nor C atom, optionally one or more carbon atoms are replaced with O.

In one embodiment, the compound is HOR₉ with R₉ being selected fromlinear or branched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl,C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy,C₇-C₁₄-arylalkoxy and C₉-C₁₅-alkenylarylalkoxy, preferably R₉ is linearor branched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl,C₃-C₈-cycloalkyl, preferably C₄-C₈-cycloalkyl, more preferablyC₄-C₆-cycloalkyl, and most preferably C₅- or C₆-cycloalkyl, e.g.C₆-cycloalkyl, and C₆-C₁₄-aryl.

Alternatively, the compound is HNR₁₀R₁₁ with R₁₀ and R₁₁ beingindependently selected from H, linear or branched C₁-C₈-alkyl,C₃-C₈-cycloalkyl, C₆-C₁₄-aryl, or R₁₀ and R₁₁ form a C₃-C₆-alicyclicsystem together with the connecting N atom, optionally one or morecarbon atoms are replaced with O, preferably R₁₀ and R₁₁ form aC₅-C₆-alicyclic system together with the connecting N atom and one ormore carbon atoms are replaced with O.

Preferably, the compound is HNR₁₀R₁₁ with R₁₀ and R₁₁ forming aC₅-C₆-alicyclic system, preferably a C₆-alicyclic system, together withthe connecting N atom and one or more carbon atoms, preferably onecarbon atom, is/are replaced with O.

For example, the compound is morpholine.

The further step of reacting the aryl oxirane to the correspondingα-functionalized ketone can be carried out over a wide temperaturerange. For example, this step is carried out at a temperature of atleast 30° C., preferably in the range from 30 to 120° C., morepreferably in the range from 40 to 100° C., and most preferably in therange from 40 to 90° C.

It is further appreciated that the further step of reacting the aryloxirane to the corresponding α-functionalized ketone can be carried outin an organic solvent. Preferably the organic solvent is selected fromthe group comprising methanol, ethanol, n-propanol, tert.-butanol,dichloromethane, tetrachloroethylene, tetrahydrofuran, ethyl acetate,acetone, N,N-dimethylformamide, dimethyl sulfoxide, dioxane, such as1,3-dioxane or 1,4-dioxane, 1,2-dimethoxyethane, diethyleneglycoldimethyl ether, triethyleneglycol dimethyl ether and mixtures thereof.

If the base is provided in an organic solvent, the organic solvent ispreferably the same as used in the process.

The further step of reacting the aryl oxirane to the correspondingα-functionalized ketone is carried out by mixing the components, i.e.the aryl oxirane, the phase-transfer catalyst, the base selected fromthe group comprising alkali metal hydroxide, earth alkali metalhydroxide, alkali metal C₁-C₈-alkoxide, earth alkali metalC₁-C₈-alkoxide and mixtures and the compound selected from HOR₉, HNHR₉or HNR₁₀R₁₁ with R₉, R₁₀ and R₁₁ being independently selected from H,linear or branched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl,C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy,C₆-C₁₄-aryl, C₇-C₁₄-arylalkyl, C₇-C₁₄-arylalkoxy,C₉-C₁₅-alkenylarylalkoxy, C₉-C₁₅-alkenylarylalkyl; or R₁₀ and R₁₁ form aC₃-C₉-alicyclic system together with the connecting N or C atom,optionally one or more carbon atoms are replaced with O. The skilled manwill adapt the mixing conditions (such as the configuration of mixingtools and mixing speed) according to his process equipment.

It has been found that the sequence of addition of the reagents isunimportant for the success of the reaction. Thus, the aryl oxirane, thephase-transfer catalyst, the base selected from the group comprisingalkali metal hydroxide, earth alkali metal hydroxide, alkali metalC₁-C₈-alkoxide, earth alkali metal C₁-C₈-alkoxide and mixtures and thecompound selected from HOR₉, HNHR₉ or HNR₁₀R₁₁ with R₉, R₁₀ and R₁₁being independently selected from H, linear or branched C₁-C₈-alkyl,linear or branched C₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy, C₆-C₁₄-aryl, C₇-C₁₅-arylalkyl,C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, C₉-C₁₅-alkenylarylalkyl; orR₁₀ and R₁₁ form a C₃-C₉-alicyclic system together with the connecting Nor C atom, optionally one or more carbon atoms are replaced with O, canbe contacted in any order.

It is appreciated that the step of reacting the aryl oxirane underphase-transfer conditions with a base selected from the group comprisingalkali metal hydroxide, earth alkali metal hydroxide, alkali metalC₁-C₈-alkoxide, earth alkali metal C₁-C₈-alkoxide and mixtures and acompound selected from HOR₉, HNHR₉ or HNR₁₀R₁₁ with R₉, R₁₀ and R₁₁being independently selected from H, linear or branched C₁-C₈-alkyl,linear or branched C₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy, C₆-C₁₄-aryl, C₇-C₁₅-arylalkyl,C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, C₉-C₁₅-alkenylarylalkyl; orR₁₀ and R₁₁ form a C₃-C₉-alicyclic system together with the connecting Nor C atom, optionally one or more carbon atoms are replaced with O,results in the corresponding α-functionalized ketone.

Subsequent to the step of reacting the aryl oxirane, the process maycomprise further steps for isolating and/or purifying the obtainedα-functionalized ketone.

For example, the process may further comprise a step of

-   -   i) separating the obtained α-functionalized ketone from the        organic phase, and/or    -   ii) taking up the obtained α-functionalized ketone in water and        extracting the obtained aqueous phase with an organic solvent.

In one embodiment, the process further comprises the steps of

-   -   i) separating the obtained α-functionalized ketone from the        organic phase, and    -   ii) taking up the obtained α-functionalized ketone in water and        extracting the obtained aqueous phase with an organic solvent.

Additionally, the process may further comprise a step of drying theobtained α-functionalized ketone.

Alternatively, the process comprises a further step of contacting theα-functionalized alkyl aryl ketal obtained by the process with an acidobtaining thereby the corresponding α-functionalized ketone.

It is appreciated that the acid is not restricted to a specific acid,but it is preferred that the acid has a pKa value below 5, morepreferably in the range from −10 to 10, and most preferably in the rangefrom −8 to 5.

In one embodiment, the acid is preferably selected from the groupcomprising hydrochloric acid, acetic acid, phosphoric acid, sulfuricacid, citric acid, toluene sulfonic acid, methane sulfonic acid,chloroacetic acid, trichloroacetic acid, tartaric acid, succinic acid,maleic acid, fumaric acid, lactic acid, malic acid, propionic acid,butyric acid and mixtures thereof. For example, the acid is selectedfrom hydrochloric acid, acetic acid, phosphoric acid, sulfuric acid,citric acid and mixtures thereof. In one embodiment, the acid ishydrochloric acid.

The acid can be added as such into the process. Alternatively, the acidis in form of an aqueous solution or the acid is provided in an organicsolvent, preferably the organic solvent is selected from the groupcomprising methanol, ethanol, n-propanol, tert.-butanol,dichloromethane, tetrachloroethylene, tetrahydrofuran, ethyl acetate,acetone, N,N-dimethylformamide, dimethyl sulfoxide, dioxane, such as1,3-dioxane or 1,4-dioxane, 1,2-dimethoxyethane, diethyleneglycoldimethyl ether, triethyleneglycol dimethyl ether and mixtures thereof.Preferably, the acid is provided in form of an aqueous solution and thusis in form of a dilute aqueous acid. This is advantageous as thereaction to enol ethers can be avoided.

The subsequent step of reacting the α-functionalized alkyl aryl ketal tothe corresponding α-functionalized ketone can be carried out over a widetemperature range. For example, this step is carried out at atemperature in the range from 0 to 120° C., preferably in the range from12 to 80° C., more preferably in the range from 15 to 50° C., and mostpreferably in the range from 15 to 30° C.

Preferably, this step is carried out at room temperature, i.e. at atemperature of about 21° C. (±2° C.).

It is further appreciated that the subsequent step of reacting theα-functionalized alkyl aryl ketal to the corresponding α-functionalizedketone can be carried out in an organic solvent. Preferably the organicsolvent is selected from the group comprising methanol, ethanol,n-propanol, tert.-butanol, dichloromethane, tetrachloroethylene,tetrahydrofuran, ethyl acetate, acetone, N,N-dimethylformamide, dimethylsulfoxide, dioxane, such as 1,3-dioxane or 1,4-dioxane,1,2-dimethoxyethane, diethyleneglycol dimethyl ether, triethyleneglycoldimethyl ether and mixtures thereof.

If the acid is provided in an organic solvent, the organic solvents arepreferably the same.

The step of reacting the α-functionalized alkyl aryl ketal to thecorresponding α-functionalized ketone is carried out by mixing thecomponents, i.e. the α-functionalized alkyl aryl ketal and the acid and,if present, the organic solvent. The skilled man will adapt the mixingconditions (such as the configuration of mixing tools and mixing speed)according to his process equipment.

It has been found that the sequence of addition of the reagents isimportant for the success of this reaction step. The best yields areobtained when the α-functionalized alkyl aryl ketal and, if present, theorganic solvent are contacted first and the acid is metered in.

Subsequent to the step of reacting the α-functionalized alkyl arylketal, the process may comprise further steps for isolating and/orpurifying the obtained α-functionalized ketone.

For example, the process may further comprise a step of

-   -   i) separating the obtained α-functionalized ketone from the        organic phase, and/or    -   ii) taking up the obtained α-functionalized ketone in water and        extracting the obtained aqueous phase with an organic solvent.

In one embodiment, the process further comprises the steps of

-   -   i) separating the obtained α-functionalized ketone from the        organic phase, and    -   ii) taking up the obtained α-functionalized ketone in water and        extracting the obtained aqueous phase with an organic solvent.

Additionally, the process may further comprise a step of drying theobtained α-functionalized ketone.

It is appreciated that an α-functionalized ketone of the general formulaII is obtained by further reacting the aryl oxirane or α-functionalizedalkyl aryl ketal,

wherein R₁, R₂, R₃, R₄, R₅, R₆ and R₇ are as defined above; and Z isselected from OR₉, NHR₉ and NR₁₀R₁₁ with R₉, R₁₀ and R₁₁ beingindependently selected from H, linear or branched C₁-C₈-alkyl, linear orbranched C₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy, C₆-C₁₄-aryl, C₇-C₁₅-arylalkyl,C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, C₉-C₁₅-alkenylarylalkyl; orR₁₀ and R₁₁ form a C₃-C₉-alicyclic system together with the connecting Nor C atom, optionally one or more carbon atoms are replaced with O.

In one embodiment, Z is OR₉ with R₉ being selected from H, linear orbranched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl, C₁-C₈-alkoxy,C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxyand C₉-C₁₅-alkenylarylalkoxy, preferably R₉ is H or Z is NR₁₀R₁₁ withR₁₀ and R₁₁ being independently selected from H, linear or branchedC₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₆-C₁₄-aryl, or R₁₀ and R₁₁ form aC₃-C₆-alicyclic system together with the connecting N atom, optionallyone or more carbon atoms are replaced with O, preferably R₁₀ and R₁₁form a C₅-C₆-alicyclic system together with the connecting N atom andone or more carbon atoms are replaced with O.

Preferably, Z is OR₉ with R₉ being H or NR₁₀R₁₁ with R₁₀ and R₁₁ forminga C₅-C₆-alicyclic system, preferably a C₆-alicyclic system, togetherwith the connecting N atom and one or more carbon atoms, preferably onecarbon atom, is/are replaced with O.

With regard to the definition of R₁, R₂, R₃, R₄, R₅, R₆, and R₇ andpreferred embodiments thereof, reference is made to the statementsprovided above when discussing the technical details of the process andthe alkyl aryl ketone of the general formula I used as starting materialin the process of the present invention.

An especially preferred α-functionalized ketone of the general formulaII obtained by the process is a ketone, wherein R₁ and R₂ are the sameand are selected from linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl; R₃, R₄, R₅, R₆ and R₇ are the same andare H, and Z is OR₉ with R₉ being H.

For example, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare C₁-alkyl; R₃, R₄, R₅, R₆ and R₇ are the same and are H, and Z is OR₉with R₉ being H.

Alternatively, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ formC₃-C₁₂-cycloalkyl, preferably C₄-C₁₀-cycloalkyl, more preferablyC₄-C₈-cycloalkyl, even more preferably C₄-C₆-cycloalkyl, and mostpreferably C₅- or C₆-cycloalkyl, e.g. C₆-cycloalkyl, together with theconnecting C atom; R₄, R₅, R₆ and R₇ are the same and are H, and Z isOR₉ with R₉ being H.

Alternatively, the α-functionalized ketone of the general formula I is aketone, wherein R₁ and R₂ are the same and are selected from linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl; R₄, R₅,R₆ and R₇ are the same and are H, and Z is NR₁₀R₁₁ with R₁₀ and R₁₁forming a C₅-C₆-alicyclic system, preferably a C₆-alicyclic system.

Alternatively, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare selected from linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl; R₄, R₅, R₆ and R₇ are the same and are H,and Z is NR₁₀R₁₁ with R₁₀ and R₁₁ forming a C₅-C₆-alicyclic system,preferably a C₆-alicyclic system, together with the connecting N atomand one or more, preferably one, carbon atoms are replaced with O.

For example, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare C₁-alkyl; R₄, R₅, R₆ and R₇ are the same and are H, and Z is NR₁₀R₁₁with R₁₀ and R₁₁ forming a C₅-C₆-alicyclic system, preferably aC₆-alicyclic system, together with the connecting N atom and one ormore, preferably one, carbon atoms are replaced with O.

Alternatively, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare selected from linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl; R₄, R₅, R₆ and R₇ are different and oneof them, preferably R₅, is linear or branched C₂-C₈-alkenyl, preferablylinear or branched C₂-C₆-alkenyl and most preferably C₂-C₃-alkenyl, e.g.C₂-alkenyl; and the remaining ones are H and Z is OR₉ with R₉ being H.

For example, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare C₁-alkyl; R₄, R₅, R₆ and R₇ are different and one of them,preferably R₅, is linear or branched C₂-C₈-alkenyl, preferably linear orbranched C₂-C₆-alkenyl and most preferably C₂-C₃-alkenyl, e.g.C₂-alkenyl; and the remaining ones are H and Z is OR₉ with R₉ being H.

Alternatively, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare selected from linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl; R₄, R₅, R₆ and R₇ are different and oneof them, preferably R₅, is linear or branched C₂-C₈-alkenyl, preferablylinear or branched C₂-C₆-alkenyl and most preferably C₂-C₃-alkenyl, e.g.C₂-alkenyl; and the remaining ones are H and Z is NR₁₀R₁₁ with R₁₀ andR₁₁ forming a C₅-C₆-alicyclic system, preferably a C₆-alicyclic system,together with the connecting N atom and one or more, preferably one,carbon atoms are replaced with O.

For example, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare C₁-alkyl; R₄, R₅, R₆ and R₇ are different and one of them,preferably R₅, is linear or branched C₂-C₈-alkenyl, preferably linear orbranched C₂-C₆-alkenyl and most preferably C₂-C₃-alkenyl, e.g.C₂-alkenyl; and the remaining ones are H and Z is NR₁₀R₁₁ with R₁₀ andR₁₁ forming a C₅-C₆-alicyclic system, preferably a C₆-alicyclic system,together with the connecting N atom and one or more, preferably one,carbon atoms are replaced with O.

Alternatively, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare selected from linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl; R₄, R₅, R₆ and R₇ are different and oneof them, preferably R₅, is SR₈ with R₈ being selected from linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl; and theremaining ones are H and Z is OR₉ with R₉ being H.

For example, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare C₁-alkyl; R₄, R₅, R₆ and R₇ are different and one of them,preferably R₅, is SR₈ with R₈ being selected from linear or branchedC₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear or branchedC₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear or branchedC₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferably linearC₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl; and theremaining ones are H and Z is OR₉ with R₉ being H.

Alternatively, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare selected from linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl; R₄, R₅, R₆ and R₇ are different and oneof them, preferably R₅, is SR₈ with R₈ being selected from linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl; and theremaining ones are H and Z is NR₁₀R₁₁ with R₁₀ and R₁₁ forming aC₅-C₆-alicyclic system, preferably a C₆-alicyclic system, together withthe connecting N atom and one or more, preferably one, carbon atoms arereplaced with O.

For example, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare C₁-alkyl; R₄, R₅, R₆ and R₇ are different and one of them,preferably R₅, is SR₈ with R₈ being selected from linear or branchedC₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear or branchedC₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear or branchedC₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferably linearC₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl; and theremaining ones are H and Z is NR₁₀R₁₁ with R₁₀ and R₁₁ forming aC₅-C₆-alicyclic system, preferably a C₆-alicyclic system, together withthe connecting N atom and one or more, preferably one, carbon atoms arereplaced with O.

Alternatively, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare selected from linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl; R₃, R₄, R₅, R₆ and R₇ are different andone of them is C₂-C₈-alkenyloxy, preferably C₂-C₆-alkenyloxy and mostpreferably C₃-C₅-alkenyloxy, e.g. C₃- or C₄-alkenyloxy, especiallyC₃-alkenyloxy; and two of the remaining ones are H and two of theremaining ones are linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl; and Z is OR₉ with R₉ being H.

For example, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare C₁-alkyl; R₃, R₄, R₅, R₆ and R₇ are different and one of them,preferably R₅, is C₂-C₈-alkenyloxy, preferably C₂-C₆-alkenyloxy and mostpreferably C₃-C₅-alkenyloxy, e.g. C₃- or C₄-alkenyloxy, especiallyC₃-alkenyloxy; and two of the remaining ones, preferably R₃ and R₇, areH and two of the remaining ones, preferably R₄ and R₆, are linear orbranched C₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear orbranched C₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear orbranched C₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferablylinear C₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl,especially C₁-alkyl; and Z is OR₉ with R₉ being H.

Alternatively, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare selected from linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl; R₃, R₄, R₅, R₆ and R₇ are different andthree of them, preferably R₃ and R₄ and R₅, areC₉-C₁₅-alkenylarylalkoxy, preferably C₉-C₁₂-alkenylarylalkoxy and mostpreferably C₉-C₁₀-alkenylarylalkoxy, and the remaining ones, preferablyR₆ and R₇ are H; and Z is OR₉ with R₉ being H.

For example, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare C₁-alkyl; R₃, R₄, R₅, R₆ and R₇ are different and three of them,preferably R₃ and R₄ and R₅, are C₉-C₁₅-alkenylarylalkoxy, preferablyC₉-C₁₂-alkenylarylalkoxy and most preferably C₉-C₁₀-alkenylarylalkoxy,and the remaining ones, preferably R₆ and R₇ are H; and Z is OR₉ with R₉being H.

Alternatively, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are different andare selected from H and linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl; R₃, R₄, R₅, R₆ and R₇ are different andtwo of them, preferably R₄ and R₅, are C₁-C₈-alkoxy, preferablyC₁-C₆-alkoxy and most preferably C₁-C₃-alkoxy, especially C₁-alkoxy; andthe remaining ones, preferably R₃, R₆ and R₇, are H and Z is OR₉ with R₉being H.

For example, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are different andare H and C₂-alkyl; R₃, R₄, R₅, R₆ and R₇ are different and two of them,preferably R₄ and R₅, are C₁-C₈-alkoxy, preferably C₁-C₆-alkoxy and mostpreferably C₁-C₃-alkoxy, especially C₁-alkoxy; and the remaining ones,preferably R₃, R₆ and R₇, are H and Z is OR₉ with R₉ being H.

Alternatively, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are different andare selected from H and linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl; R₃, R₄, R₅, R₆ and R₇ are different andone of them, preferably R₅, is N(R₈)₂ with R₈ forming a C₃-C₉-alicyclicsystem, preferably a C₃-C₇-alicyclic system, more preferably aC₄-C₆-alicyclic system and most preferably a C₅- or C₆-alicyclic system,together with the connecting N atom, wherein one or more, preferablyone, carbon atoms are replaced with O; and the remaining ones,preferably R₃, R₄, R₆ and R₇, are H and Z is OR₉ with R₉ being H.

For example, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are different andare H and C₂-alkyl; R₃, R₄, R₅, R₆ and R₇ are different and one of them,preferably R₅, is N(R₈)₂ with R₈ forming a C₃-C₉-alicyclic system,preferably a C₃-C₇-alicyclic system, more preferably a C₄-C₆-alicyclicsystem and most preferably a C₅- or C₆-alicyclic system, together withthe connecting N atom, wherein one or more, preferably one, carbon atomsare replaced with O; and the remaining ones, preferably R₃, R₄, R₆ andR₇, are H and Z is OR₉ with R₉ being H.

Alternatively, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare selected from linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl; R₄ and R₅ form an aromatic systemtogether with the benzene ring of general formula I, preferably abicyclic aromatic system, most preferably naphthyl; and the remainingones are independently selected from H and linear or branchedC₁-C₈-alkyl, e.g. linear C₁-C₈-alkyl, preferably linear or branchedC₁-C₆-alkyl, e.g. linear C₁-C₆-alkyl, more preferably linear or branchedC₁-C₄-alkyl, e.g. linear C₁-C₄-alkyl, and most preferably linearC₁-C₃-alkyl, e.g. C₁- or C₂-alkyl, especially C₁-alkyl, preferably H,and Z is OR₉ with R₉ being H.

For example, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare C₁-alkyl; R₄ and R₅ form an aromatic system together with thebenzene ring of general formula I, preferably a bicyclic aromaticsystem, most preferably naphthyl; and the remaining ones are H and Z isOR₉ with R₉ being H.

Alternatively, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare selected from linear or branched C₁-C₈-alkyl, e.g. linearC₁-C₈-alkyl, preferably linear or branched C₁-C₆-alkyl, e.g. linearC₁-C₆-alkyl, more preferably linear or branched C₁-C₄-alkyl, e.g. linearC₁-C₄-alkyl, and most preferably linear C₁-C₃-alkyl, e.g. C₁- orC₂-alkyl, especially C₁-alkyl; R₄ and R₅ form an aromatic systemtogether with the benzene ring of general formula I, preferably abicyclic aromatic system, most preferably naphthyl; and one of theremaining R, preferably R₃, is linear or branched C₂-C₈-alkenyl,preferably C₂-C₆-alkenyl and most preferably C₂-C₃-alkenyl;C₂-C₈-alkenyloxy, preferably C₂-C₆-alkenyloxy and most preferablyC₃-C₅-alkenyloxy; and C₉-C₁₅-alkenylarylalkoxy, preferablyC₉-C₁₂-alkenylarylalkoxy and most preferably C₉-C₁₀-alkenylarylalkoxyand the remaining ones are H, and Z is OR₉ with R₉ being H.

For example, the α-functionalized ketone of the general formula IIobtained by the process is a ketone, wherein R₁ and R₂ are the same andare C₁-alkyl; R₄ and R₅ form an aromatic system together with thebenzene ring of general formula I, preferably a bicyclic aromaticsystem, most preferably naphthyl; and one of the remaining R, preferablyR₃, is C₉-C₁₅-alkenylarylalkoxy, preferably C₉-C₁₂-alkenylarylalkoxy andmost preferably C₉-C₁₀-alkenylarylalkoxy and the remaining ones are H,and Z is OR₉ with R₉ being H.

A further aspect of the present invention refers to the aryl oxirane orα-functionalized alkyl aryl ketal obtained by the process as definedherein.

Accordingly, the aryl oxirane or α-functionalized alkyl aryl ketal areobtained by a process for reacting an alkyl aryl ketone of the generalformula I,

wherein R₁ and R₂ are the same or different and are independentlyselected from H, linear or branched C₁-C₈-alkyl, C₃-C₈-cycloalkyl,linear or branched C₂-C₈-alkenyl, C₅-C₈-cycloalkenyl, linear or branchedC₂-C₈-alkynyl, C₆-C₁₄-aryl or form C₃-C₁₂-cycloalkyl orC₅-C₁₂-cycloalkenyl together with the connecting C atom;

R₃, R₄, R₅, R₆ and R₇ are the same or different and are independentlyselected from H, linear or branched C₁-C₈-alkyl, linear or branchedC₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl,C₆-C₁₄-aryl, C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxy,C₉-C₁₅-alkenylarylalkoxy, N(R₈)₂ or SR₈ with R₈ being selected fromlinear or branched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl,C₆-C₁₄-aryl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, or R₈form a C₃-C₉-alicyclic system together with the connecting N atom,optionally one or more carbon atoms are replaced with O, or two adjacentR form an aromatic system together with the benzene ring of formula I;

with an at least partially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene,and a base selected from alkali metal C₁-C₈-alkoxide, earth alkali metalC₁-C₈-alkoxide and mixtures thereof, obtaining thereby the correspondingaryl oxirane or α-functionalized alkyl aryl ketal.

With regard to the definition of the process, R₁, R₂, R₃, R₄, R₅, R₆,and R₇ and preferred embodiments thereof, reference is made to thestatements provided above when discussing the technical details of theprocess and the alkyl aryl ketone of the general formula I used asstarting material in the process of the present invention.

Another aspect of the present invention refers to the α-functionalizedketone of the general formula II obtained by the process as definedherein.

Accordingly, the α-functionalized ketone of the general formula II isobtained by a process for reacting an alkyl aryl ketone of the generalformula I,

wherein R₁ and R₂ are the same or different and are independentlyselected from H, linear or branched C₁-C₈-alkyl, C₃-C₈-cycloalkyl,linear or branched C₂-C₈-alkenyl, C₅-C₈-cycloalkenyl, linear or branchedC₂-C₈-alkynyl, C₆-C₁₄-aryl or form C₃-C₁₂-cycloalkyl orC₅-C₁₂-cycloalkenyl together with the connecting C atom;

R₃, R₄, R₅, R₆ and R₇ are the same or different and are independentlyselected from H, linear or branched C₁-C₈-alkyl, linear or branchedC₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl,C₆-C₁₄-aryl, C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxy,C₉-C₁₅-alkenylarylalkoxy, N(R₈)₂ or SR₈ with R₈ being selected fromlinear or branched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl,C₆-C₁₄-aryl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, or R₈form a C₃-C₉-alicyclic system together with the connecting N atom,optionally one or more carbon atoms are replaced with O, or two adjacentR form an aromatic system together with the benzene ring of formula I;

with an at least partially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene,and a base selected from alkali metal C₁-C₈-alkoxide, earth alkali metalC₁-C₈-alkoxide and mixtures thereof, obtaining thereby the correspondingaryl oxirane, and further contacting the aryl oxirane obtained by theprocess under phase-transfer conditions with a base selected from thegroup comprising alkali metal hydroxide, earth alkali metal hydroxide,alkali metal C₁-C₈-alkoxide, earth alkali metal C₁-C₈-alkoxide andmixtures and a compound selected from HOR₉, HNHR₉ or HNR₁₀R₁₁ with R₉,R₁₀ and R₁₁ being independently selected from H, linear or branchedC₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl, C₁-C₈-alkoxy,C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy, C₆-C₁₄-aryl,C₇-C₁₅-arylalkyl, C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy,C₉-C₁₅-alkenylarylalkyl; or R₁₀ and R₁₁ form a C₃-C₉-alicyclic systemtogether with the connecting N or C atom, optionally one or more carbonatoms are replaced with O; obtaining thereby the correspondingα-functionalized ketone.

Alternatively, the α-functionalized ketone of the general formula II isobtained by a process for reacting an alkyl aryl ketone of the generalformula I,

wherein R₁ and R₂ are the same or different and are independentlyselected from H, linear or branched C₁-C₈-alkyl, C₃-C₈-cycloalkyl,linear or branched C₂-C₈-alkenyl, C₅-C₈-cycloalkenyl, linear or branchedC₂-C₈-alkynyl, C₆-C₁₄-aryl or form C₃-C₁₂-cycloalkyl orC₅-C₁₂-cycloalkenyl together with the connecting C atom;

R₃, R₄, R₅, R₆ and R₇ are the same or different and are independentlyselected from H, linear or branched C₁-C₈-alkyl, linear or branchedC₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl,C₆-C₁₄-aryl, C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxy,C₉-C₁₅-alkenylarylalkoxy, N(R₈)₂ or SR₈ with R₈ being selected fromlinear or branched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl,C₆-C₁₄-aryl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, or R₈form a C₃-C₉-alicyclic system together with the connecting N atom,optionally one or more carbon atoms are replaced with O, or two adjacentR form an aromatic system together with the benzene ring of formula I;

with an at least partially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene,and a base selected from alkali metal C₁-C₈-alkoxide, earth alkali metalC₁-C₈-alkoxide and mixtures thereof, obtaining thereby the correspondingα-functionalized ketal, and further contacting the α-functionalizedalkyl aryl ketal obtained by the process with an acid, preferably anacid selected from the group comprising hydrochloric acid, acetic acid,phosphoric acid, sulfuric acid, citric acid, toluene sulfonic acid,methanesulfonic acid, chloroacetic acid, trichloroacetic acid, tartaricacid, succinic acid, maleic acid, fumaric acid, lactic acid, malic acid,propionic acid, butyric acid and mixtures thereof; obtaining thereby thecorresponding α-functionalized ketone.

With regard to the definition of the process, the aryl oxirane, theα-functionalized alkyl aryl ketal the α-functionalized ketone andpreferred embodiments thereof, reference is made to the statementsprovided above when discussing the technical details of the process ofthe present invention.

The scope and interest of the invention will be better understood basedon the following examples which are intended to illustrate certainembodiments of the invention and are non-limitative.

EXAMPLES Example 1: Preparation of2-methoxy-3,3-dimethyl-2-(4-methylthiophenyl)oxirane

A mixture of sodium methoxide (30% in methanol, 8.34 g, 154 mmol),methanol (15.5 mL), 2-methyl-1-(4-methylthiophenyl)propan-1-one (3.00 g,15.4 mmol) and hexachloroethane (5.48 g, 23.2 mmol) was stirredovernight at room temperature. The solvent was evaporated, the residuetaken up with water (25 mL) and extracted with ethyl acetate (3×20 mL).The combined organic phases were washed with brine (30 mL), dried overNa₂SO₄ and the solvent was evaporated.2-methoxy-3,3-dimethyl-2-(4-methylthiophenyl)oxirane was obtained as ayellow oil (2.86 g, 12.8 mmol, 82% yield).

¹H-NMR (400.1 MHz, CDCl₃): δ=1.03 (s, 3H), 1.55 (s, 1H), 2.52 (s, 3H),3.23 (s, 3H), 7.24-7.31 (m, 2H), 7.34-7.43 (m, 2H) ppm.

¹³C-NMR (100.6 MHz, CDCl₃): δ=15.5, 19.8, 20.0, 52.6, 67.3, 124.7,125.8, 128.4, 130.3, 131.4, 139.0 ppm.

Example 2: Preparation of2-methyl-1-(4-methylthiophenyl)-2-morpholino-propan-1-one

A mixture of 2-methoxy-3,3-dimethyl-2-(4-methylthiophenyl)oxirane (0.13g, 0.58 mmol), morpholine (2.27 g, 26.1 mmol), sodium hydroxide solution(50%, 0.28 g, 3.5 mmol) and tetrabutylammonium hydrogensulfate (0.01 g,0.03 mmol) was stirred under reflux for 8 h. The reaction mixture wascooled down to room temperature, the solvent was evaporated underreduced pressure and the residue was taken up with water (10 mL). Thephases were separated and the pH of the aqueous layer was adjusted to 7with saturated ammonium chloride solution. The aqueous layer wasextracted with ethyl acetate (3×5 mL). The combined organic layers werewashed with brine (10 mL), dried over Na₂SO₄ and the solvent wasevaporated. 2-methyl-1-(4-methylthiophenyl)-2-morpholino-propan-1-onewas obtained as a colorless oil (70 mg, 0.25 mmol, 43% yield).

¹H-NMR (400.1 MHz, CDCl₃): δ=1.31 (s, 6H), 2.53 (s, 3H), 2.55-2.61 (m,4H), 3.66-3.73 (m, 4H), 7.20-7.26 (m, 2H), 8.49-8.54 (m, 2H) ppm.¹³C-NMR (100.6 MHz, CDCl₃): δ=14.4, 20.4, 47.2, 67.3, 68.3, 124.3,130.3, 131.8, 144.9, 201.9 ppm.

Example 3: Preparation of 2,2-diethyl-3-methoxy-3-phenyl-oxirane

A mixture of sodium methoxide (30% in methanol, 12.3 g, 87.1 mmol),methanol (11.5 mL), 2-ethyl-1-phenylbutan-1-one (2.00 g, 11.4 mmol) andhexachloroethane (2.96 g, 12.5 mmol) was stirred overnight at roomtemperature. The solvent was evaporated, the residue taken up with water(50 mL) and extracted with ethyl acetate (3×20 mL). The combined organicphases were washed with brine (50 mL), dried over Na₂SO₄ and the solventwas evaporated.

The crude product was purified by flash chromatography [basic aluminumoxide, c-C₆H₁₂/AcOEt, 1:1 v:v]. 2,2-diethyl-3-methoxy-3-phenyl-oxiranewas obtained as a colorless oil (2.26 g, 11.0 mmol, 96% yield).

¹H-NMR (400.1 MHz, CDCl₃): δ=0.79-0.82 (t, 3H), 1.06-1.10 (t, 3H),1.16-1.37 (m, 2H), 1.79-1.91 (m, 1H), 1.94-2.04 (m, 1H), 3.21 (s, 3H),7.34-7.43 (m, 3H), 7.45-7.50 (m, 3H) ppm. ¹³C-NMR (100.6 MHz, CDCl₃):δ=8.6, 9.3, 22.3, 22.5, 52.4, 73.7, 91.9, 127.9, 128.0, 128.3, 134.9ppm.

Example 4: Preparation of4-(1,1-dimethoxy-2-hydroxybutyl)-1,2-dimethoxybenzene

A mixture of sodium methoxide (30% in methanol, 15.82 g, 87.87 mmol),methanol (14.5 mL), 4-butyryl-1,2-dimethoxybenzene (3.00 g, 14.4 mmol)and hexachloroethane (3.79 g, 16.0 mmol) was stirred overnight at roomtemperature. The solvent was evaporated, the residue taken up with water(25 mL) and extracted with ethyl acetate (3×20 mL). The combined organicphases were washed with brine (30 mL), dried over Na₂SO₄ and the solventwas evaporated. 4-(1,1-Dimethoxy-2-hydroxybutyl)-1,2-dimethoxybenzenewas obtained as a yellow oil (2.97 g, 10.9 mmol, 79% yield). ¹H-NMR(400.1 MHz, CDCl₃): δ=0.92-0.96 (t, 3H), 0.98-1.11 (m, 1H), 1.46-1.56(m, 1H), 2.19-2.24 (dd, 1H), 3.24 (s, 3H), 3.36 (s, 3H), 3.77-3.85 (m,1H), 3.90 (s, 3H), 3.91 (s, 3H), 6.85-6.89 (m, 1H), 6.99-7.06 (m, 2H)ppm. ¹³C-NMR (100.6 MHz, CDCl₃): δ=10.9, 24.0, 49.3, 49.8, 55.8, 55.9,76.3, 103.3, 110.3, 111.3, 120.4, 130.3, 148.3, 148.7 ppm.

Example 5: Preparation of 1-(3,4-dimethoxyphenyl)-2-hydroxy-butan-1-one

1-(3,4-dimethoxyphenyl)-1,1-dimethoxy-butan-2-ol (0.50 g, 1.9 mmol) wasdissolved in 1,4-dioxane (8 mL). Hydrochloric acid (1 M, 0.14 g, 3.7mmol) was added and the reaction mixture was stirred for 6 h at roomtemperature. Afterwards, the reaction mixture was extracted with ethylacetate (3×50 mL). The combined organic layers were washed with brine(50 mL) and the solvent was removed under reduced pressure. The crudeproduct was purified by preparative thin layer chromatography on silicagel [c-C₆H₁₂/AcOEt, 2:1 v:v].1-(3,4-dimethoxyphenyl)-2-hydroxy-butan-1-one was obtained as acolorless oil (0.28 g, 1.0 mmol, 55% yield).

¹H-NMR (400.1 MHz, CDCl₃): δ=0.94-0.97 (t, 3H), 1.57-1.73 (m, 1H),1.90-2.01 (m, 1H), 3.73-3.74 (d, 1H), 3.95 (s, 3H), 3.97 (s, 3H),4.98-5.06 (m, 1H), 6.91-6.95 (m, 1H), 7.51-7.54 (m, 2H) ppm. ¹³C-NMR(100.6 MHz, CDCl₃): δ=9.0, 29.5, 56.0, 56.1, 73.5, 110.2, 110.6, 123.2,126.7, 149.4, 154.0, 200.4 ppm.

Example 6: Preparation of4-(1,1-dimethoxy-2-hydroxybutyl)-phenylmorpholine

A mixture of sodium methoxide (30% in methanol, 4.71 g, 26.1 mmol),methanol (4.5 mL), 4-butyryl-phenylmorpholine (1.00 g, 4.29 mmol) andhexachloroethane (3.79 g, 4.76 mmol) was stirred under reflux for 6 h.The solvent was evaporated, the residue taken up with water (25 mL) andextracted with ethyl acetate (3×20 mL). The combined organic phases werewashed with brine (30 mL), dried over Na₂SO₄ and the solvent wasevaporated. 4-(1,1-Dimethoxy-2-hydroxybutyl)-phenylmorpholine wasobtained in as a yellow oil (1.04 g, 3.52 mmol, 92% yield).

¹H-NMR (400.1 MHz, CDCl₃): δ=0.91-0.95 (t, 3H), 0.96-1.06 (m, 1H),1.46-1.55 (m, 1H), 3.18-3.22 (m, 5H; two superimposed signals), 3.23 (s,3H), 3.35 (s, 3H), 3.79-3.84 (m, 1H), 3.87-3.89 (m, 4H), 6.88-6.91 (m,2H), 7.34-7.39 (m, 2H) ppm.

Example 7: Preparation of 2-hydroxy-1-(4-morpholinophenyl)butan-1-one

1,1-dimethoxy-1-(4-morpholinophenyl)butan-2-ol (0.50 g, 1.7 mmol) wasdissolved in 1,4-dioxane (7.5 mL). Hydrochloric acid (1 M, 0.13 g, 3.4mmol) was added and the reaction mixture was stirred for 6 h at roomtemperature. Afterwards, the reaction mixture was extracted with ethylacetate (3×50 mL). The combined organic layers were washed with brine(50 mL) and the solvent was removed under reduced pressure.2-hydroxy-1-(4-morpholinophenyl)butan-1-one was obtained as a yellow oil(0.31 g, 1.0 mmol, 60% yield).

¹H-NMR (400.1 MHz, CDCl₃): δ=0.89-0.92 (t, 3H), 1.53-1.65 (m, 1H),1.82-1.96 (m, 1H), 3.29-3.31 (m, 4H), 3.42 (wide s, 1H), 3.81-3.83 (m,4H), 4.91-4.97 (m, 1H), 6.82-6.89 (m, 1H), 7.77-7.86 (m, 2H) ppm.¹³C-NMR (100.6 MHz, CDCl₃): δ=8.9, 29.3, 47.4, 66.5, 73.3, 113.1, 122.8,123.8, 130.3, 130.6, 154.7, 199.7 ppm.

1: A process comprising reacting an alkyl aryl ketone of the generalformula I,

wherein R₁ and R₂ are the same or different and are independentlyselected from H, linear or branched C₁-C₈-alkyl, C₃-C₈-cycloalkyl,linear or branched C₂-C₈-alkenyl, C₅-C₈-cycloalkenyl, linear or branchedC₂-C₈-alkynyl, C₆-C₁₄-aryl or form C₃-C₁₂-cycloalkyl orC₅-C₁₂-cycloalkenyl together with the connecting C atom; R₃, R₄, R₅, R₆and R₇ are the same or different and are independently selected from H,linear or branched C₁-C₈-alkyl, linear or branched C₂-C₈-alkenyl,C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl, C₆-C₁₄-aryl,C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, N(R₈)₂or SR₈ with R₈ being selected from linear or branched C₁-C₈-alkyl,linear or branched C₂-C₈-alkenyl, C₆-C₁₄-aryl, C₁-C₈-alkoxy,C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy,C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, or R₈ form aC₃-C₉-alicyclic system together with the connecting N atom, optionallyone or more carbon atoms are replaced with O, or two adjacent R form anaromatic system together with the benzene ring of formula I; with an atleast partially halogenated C₂-C₈-alkane and/or C₂-C₈-alkene, and a baseselected from alkali metal C₁-C₈-alkoxide, earth alkali metalC₁-C₈-alkoxide and mixtures thereof, to obtain a corresponding aryloxirane or α-functionalized alkyl aryl ketal. 2: The process accordingto claim 1, wherein R₁ and R₂ are the same. 3: The process according toclaim 2, wherein R₁ and R₂ are selected from H and linear or branchedC₁-C₈-alkyl. 4: The process according to claim 1, wherein R₁ and R₂ aredifferent and are independently selected from H and linear or branchedC₁-C₈-alkyl. 5: The process according to claim 1, wherein R₁ and R₂ forma C₄-C₁₀-cycloalkyl together with the connecting C atom. 6: The processaccording to claim 1, wherein R₃, R₄, R₅, R₆ and R₇ are the same. 7: Theprocess according to claim 6, wherein R₃, R₄, R₅, R₆ and R₇ are selectedfrom H and linear or branched C₁-C₈-alkyl. 8: The process according toclaim 1, wherein R₃, R₄, R₅, R₆ and R₇ are different and at least one ofthem is selected from linear or branched C₁-C₈-alkyl, linear or branchedC₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₉-C₁₅-alkenylarylalkoxyor N(R₈)₂ or SR₈, wherein R₈ is selected from linear or branchedC₁-C₈-alkyl or linear or branched C₂-C₈-alkenyl or R₈ form aC₃-C₉-alicyclic system together with the connecting N atom. 9: Theprocess according to claim 1, wherein one of R₃, R₄, R₅, R₆ and R₇ islinear or branched C₂-C₈-alkenyl C₂-C₈-alkenyloxy,C₉-C₁₅-alkenylarylalkoxy, or N(R₈)₂ or SR₈ with R₈ being selected fromlinear or branched C₁-C₈-alkyl or linear or branched C₂-C₈-alkenyl or R₈form a C₃-C₉-alicyclic system together with the connecting N atom; andthe remaining ones are independently selected from H and linear orbranched C₁-C₈-alkyl. 10: The process according to claim 1, wherein twoor three of R₃, R₄, R₅, R₆ and R₇ are linear or branched C₂-C₈-alkenylC₁-C₈-alkoxy, C₂-C₈-alkenyloxy, and C₉-C₁₅-alkenylarylalkoxy, and theremaining ones are independently selected from H and linear or branchedC₁-C₈-alkyl. 11: The process according to claim 1, wherein R₃ and R₄ orR₄ and R₅ form an aromatic system together with the benzene ring offormula I. 12: The process according to claim 11, wherein one of theremaining R is linear or branched C₂-C₈-alkenyl andC₉-C₁₅-alkenylarylalkoxy, and the remaining ones are independentlyselected from H and linear or branched C₁-C₈-alkyl. 13: The processaccording to claim 1, wherein the at least partially halogenatedC₂-C₈-alkane and/or C₂-C₈-alkene is fully halogenated. 14: The processaccording to claim 1, wherein the base is selected from sodiumC₁-C₆-alkoxide lithium C₁-C₆-alkoxide, potassium C₁-C₆-alkoxide, andmixtures thereof. 15: The process according to claim 1, wherein the baseis in form of an aqueous solution or the base is provided in an organicsolvent. 16: The process according to claim 1, wherein the process iscarried out at a temperature in the range from 0 to 120° C. 17: Theprocess according to claim 1, wherein the process is carried out in anorganic solvent. 18: The process according to claim 1, wherein theprocess comprises a further step of contacting the aryl oxirane obtainedby the process under phase-transfer conditions with a base selected fromalkali metal hydroxide, earth alkali metal hydroxide, alkali metalC₁-C₈-alkoxide, earth alkali metal C₁-C₈-alkoxide and mixtures thereofand a compound selected from HOR₉, HNHR₉ or HNR₁₀R₁₁ with R₉, R₁₀ andR₁₁ being independently selected from H, linear or branched C₁-C₈-alkyl,linear or branched C₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy, C₆-C₁₄-aryl, C₇-C₁₅-arylalkyl,C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, C₉-C₁₅-alkenylarylalkyl; orR₁₀ and R₁₁ form a C₃-C₉-alicyclic system together with the connecting Nor C atom, optionally one or more carbon atoms are replaced with O. 19:The process according to claim 18, wherein the step is carried out inthe presence of a phase-transfer catalyst. 20: The process according toclaim 1, wherein the process comprises a further step of contacting theα-functionalized alkyl aryl ketal obtained by the process with an acid.21: The process according to claim 1, wherein an α-functionalized ketoneof the general formula II is obtained,

wherein R₁, R₂, R₃, R₄, R₅, R₆ and R₇ are as defined above; and Z isselected from OR₉, NHR₉ and NR₁₀R₁₁ with R₉, R₁₀ and R₁₁ beingindependently selected from H, linear or branched C₁-C₈-alkyl, linear orbranched C₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy, C₆-C₁₄-aryl, C₇-C₁₅-arylalkyl,C₇-C₁₅-arylalkoxy, C₉-C₁₅-alkenylarylalkoxy, C₉-C₁₅-alkenylarylalkyl; orR₁₀ and R₁₁ form a C₃-C₉-alicyclic system together with the connecting Nor C atom, optionally one or more carbon atoms are replaced with O. 22:The process according to claim 21, wherein Z is OR₉ with R₉ beingselected from H, linear or branched C₁-C₈-alkyl, linear or branchedC₂-C₈-alkenyl, C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkoxy, C₇-C₁₅-arylalkoxy and C₉-C₁₅-alkenylarylalkoxy, or Zis NR₁₀R₁₁ with R₁₀ and R₁₁ being independently selected from H, linearor branched C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₆-C₁₄-aryl, or R₁₀ and R₁₁form a C₃-C₆-alicyclic system together with the connecting N atom,optionally one or more carbon atoms are replaced with O.